{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,12]],"date-time":"2026-09-12T09:26:56Z","timestamp":1789205216325,"version":"build-2803163510"},"reference-count":67,"publisher":"Springer Science and Business Media LLC","issue":"1","license":[{"start":{"date-parts":[[2017,4,6]],"date-time":"2017-04-06T00:00:00Z","timestamp":1491436800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2017,4,6]],"date-time":"2017-04-06T00:00:00Z","timestamp":1491436800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["Nat Commun"],"abstract":"<jats:title>Abstract<\/jats:title><jats:p>\u03b1-amino acids bearing aromatic side chains are important synthetic units in the synthesis of peptides and natural products. Although various \u03b2-C-H arylation methodologies for amino acid derivatives involving the assistance of directing groups have been extensively developed, syntheses that directly employ <jats:italic>N<\/jats:italic>-protected amino acids as starting materials remain rare. Herein, we report an <jats:italic>N<\/jats:italic>-acetylglycine-enabled Pd-catalysed carboxylate-directed \u03b2-C(<jats:italic>sp<\/jats:italic><jats:sup>3<\/jats:sup>)-H arylation of aliphatic acids. In this way, various non-natural amino acids can be directly prepared from phthaloylalanine in one step in good to excellent yields. Furthermore, a series of aliphatic acids have been shown to be amenable to this transformation, affording \u03b2-arylated propionic acid derivatives in moderate to good yields. More importantly, this ligand-enabled direct \u03b2-C(<jats:italic>sp<\/jats:italic><jats:sup>3<\/jats:sup>)-H arylation could be easily scaled-up to 10\u2009g under reflux conditions, highlighting the potential utility of this synthetic method.<\/jats:p>","DOI":"10.1038\/ncomms14904","type":"journal-article","created":{"date-parts":[[2017,4,6]],"date-time":"2017-04-06T12:09:53Z","timestamp":1491480593000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":100,"title":["Pd-catalysed ligand-enabled carboxylate-directed highly regioselective arylation of aliphatic acids"],"prefix":"10.1038","volume":"8","author":[{"given":"Yan","family":"Zhu","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaolan","family":"Chen","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chunchen","family":"Yuan","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Guobao","family":"Li","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jingyu","family":"Zhang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yingsheng","family":"Zhao","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2017,4,6]]},"reference":[{"key":"BFncomms14904_CR1","doi-asserted-by":"crossref","first-page":"359","DOI":"10.1038\/sj.mp.4000976","volume":"7","author":"AV Glushakov","year":"2002","unstructured":"Glushakov, A. V., Dennis, D. M. & Martynyuk, A. E. Specific inhibition of N-methyl-D-aspartate receptor function in rat hippocampal neurons by L-phenylalanine at concentrations observed during phenylketonuria. Mol. Psychiatr. 7, 359\u2013367 (2002).","journal-title":"Mol. Psychiatr."},{"key":"BFncomms14904_CR2","doi-asserted-by":"crossref","first-page":"4640","DOI":"10.1021\/jm00102a020","volume":"35","author":"GD Hartman","year":"1992","unstructured":"Hartman, G. D., Egbertson, M. S. & Lynch, R. J. Non-peptide fibrinogen receptor antagonists. 1. Discovery and design of exosite inhibitors. J. Med. Chem. 35, 4640\u20134642 (1992).","journal-title":"J. Med. Chem."},{"key":"BFncomms14904_CR3","doi-asserted-by":"crossref","first-page":"633","DOI":"10.1021\/ar000209h","volume":"34","author":"C Jia","year":"2001","unstructured":"Jia, C., Kitamura, T. & Fujiwara, Y. Catalytic functionalization of arenes and alkanes via C\u2212H bond activation. Acc. Chem. Res. 34, 633\u2013639 (2001).","journal-title":"Acc. Chem. Res."},{"key":"BFncomms14904_CR4","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1126\/science.1114731","volume":"312","author":"K Godula","year":"2006","unstructured":"Godula, K. & Sames, D. C-H bond functionalization in complex organic synthesis. Science 312, 67\u201372 (2006).","journal-title":"Science"},{"key":"BFncomms14904_CR5","doi-asserted-by":"crossref","first-page":"1147","DOI":"10.1021\/cr900184e","volume":"110","author":"TW Lyons","year":"2010","unstructured":"Lyons, T. W. & Sanford, M. S. Palladium-catalyzed ligand-directed C\u2212H functionalization reactions. Chem. Rev. 110, 1147\u20131169 (2010).","journal-title":"Chem. Rev."},{"key":"BFncomms14904_CR6","doi-asserted-by":"crossref","first-page":"788","DOI":"10.1021\/ar200185g","volume":"45","author":"KM Engle","year":"2012","unstructured":"Engle, K. M., Mei, T.-S. & Yu, J.-Q. Weak coordination as a powerful means for developing broadly useful C\u2013H functionalization reactions. Acc. Chem. Res. 45, 788\u2013802 (2012).","journal-title":"Acc. Chem. Res."},{"key":"BFncomms14904_CR7","doi-asserted-by":"crossref","first-page":"1885","DOI":"10.1039\/c1cs15013h","volume":"40","author":"L McMurray","year":"2011","unstructured":"McMurray, L., O\u2019Hara, F. & Gaunt, M. J. Weak coordination as a powerful means for developing broadly useful C\u2013H functionalization reactions. Chem. Soc. Rev. 40, 1885\u20131898 (2011).","journal-title":"Chem. Soc. Rev."},{"key":"BFncomms14904_CR8","doi-asserted-by":"crossref","first-page":"1293","DOI":"10.1021\/cr100198w","volume":"111","author":"C-L Sun","year":"2011","unstructured":"Sun, C.-L., Li, B.-J. & Shi, Z.-J. Recent developments in natural product synthesis using metal-catalysed C\u2013H bond functionalization. Chem. Rev. 111, 1293\u20131314 (2011).","journal-title":"Chem. Rev."},{"key":"BFncomms14904_CR9","doi-asserted-by":"crossref","first-page":"11726","DOI":"10.1002\/anie.201301451","volume":"52","author":"G Rouquet","year":"2013","unstructured":"Rouquet, G. & Chatani, N. Catalytic functionalization of C(sp2)-H and C(sp3)-H bonds by using bidentate directing groups. Angew. Chem., Int. Ed. 52, 11726\u201311743 (2013).","journal-title":"Angew. Chem., Int. Ed."},{"key":"BFncomms14904_CR10","doi-asserted-by":"crossref","first-page":"281","DOI":"10.1021\/ar3002798","volume":"47","author":"L Ackermann","year":"2014","unstructured":"Ackermann, L. Carboxylate-assisted ruthenium-catalyzed alkyne annulations by C\u2013H\/Het\u2013H bond functionalizations. Acc. Chem. Res. 47, 281\u2013295 (2014).","journal-title":"Acc. Chem. Res."},{"key":"BFncomms14904_CR11","doi-asserted-by":"crossref","first-page":"5215","DOI":"10.1002\/anie.200705613","volume":"47","author":"T-S Mei","year":"2008","unstructured":"Mei, T.-S., Giri, R. & Yu, J.-Q. PdII-catalyzed monoselective ortho halogenation of c-h bonds assisted by counter cations: a complementary method to directed ortho lithiation. Angew. Chem., Int. Ed. 47, 5215\u20135219 (2008).","journal-title":"Angew. Chem., Int. Ed."},{"key":"BFncomms14904_CR12","doi-asserted-by":"crossref","first-page":"14082","DOI":"10.1021\/ja8063827","volume":"130","author":"R Giri","year":"2008","unstructured":"Giri, R. & Yu, J.-Q. Synthesis of 1,2- and 1,3-dicarboxylic acids via Pd(II)-catalyzed carboxylation of aryl and vinyl C\u2212H bonds. J. Am. Chem. Soc. 130, 14082\u201314083 (2008).","journal-title":"J. Am. Chem. Soc."},{"key":"BFncomms14904_CR13","doi-asserted-by":"crossref","first-page":"5094","DOI":"10.1002\/anie.200806273","volume":"48","author":"X Chen","year":"2009","unstructured":"Chen, X., Engle, K. M. & Yu, J.-Q. Palladium(II)-catalyzed C-H activation\/C-C cross-coupling reactions: versatility and practicality. Angew. Chem., Int. Ed. 48, 5094\u20135115 (2009).","journal-title":"Angew. Chem., Int. Ed."},{"key":"BFncomms14904_CR14","doi-asserted-by":"crossref","first-page":"315","DOI":"10.1126\/science.1182512","volume":"327","author":"D-H Wang","year":"2010","unstructured":"Wang, D.-H., Engle, K. M. & Yu, J.-Q. Ligand-enabled reactivity and selectivity in a synthetically versatile aryl C\u2013H olefination. Science 327, 315\u2013319 (2010).","journal-title":"Science"},{"key":"BFncomms14904_CR15","doi-asserted-by":"crossref","first-page":"18654","DOI":"10.1002\/chem.201603263","volume":"22","author":"M Pichette Drapeau","year":"2016","unstructured":"Pichette Drapeau, M. & Goo\u00dfen, L. J. Carboxylic acids as directing groups for C-H bond fuctionalization. Chem. Eur. J. 22, 18654\u201318677 (2016).","journal-title":"Chem. Eur. J."},{"key":"BFncomms14904_CR16","doi-asserted-by":"crossref","first-page":"3510","DOI":"10.1021\/ja0701614","volume":"129","author":"R Giri","year":"2007","unstructured":"Giri, R., Maugel, N. & Yu, J.-Q. Palladium-catalyzed methylation and arylation of sp2 and sp3 C\u2212H bonds in simple carboxylic acids. J. Am. Chem. Soc. 129, 3510\u20133511 (2007).","journal-title":"J. Am. Chem. Soc."},{"key":"BFncomms14904_CR17","doi-asserted-by":"crossref","first-page":"1735","DOI":"10.1021\/cr940337h","volume":"105","author":"ME Jung","year":"2005","unstructured":"Jung, M. E. & Piizzi, G. gem-Disubstituent effect: theoretical basis and synthetic applications. Chem. Rev. 105, 1735\u20131766 (2005).","journal-title":"Chem. Rev."},{"key":"BFncomms14904_CR18","doi-asserted-by":"crossref","first-page":"5685","DOI":"10.1021\/ol0618858","volume":"8","author":"R Giri","year":"2006","unstructured":"Giri, R., Wasa, M. & Yu, J.-Q. Converting gem-dimethyl groups into cyclopropanes via Pd-catalyzed sequential C\u2212H activation and radical cyclization. Org. Lett. 8, 5685\u20135688 (2006).","journal-title":"Org. Lett."},{"key":"BFncomms14904_CR19","doi-asserted-by":"crossref","first-page":"2112","DOI":"10.1002\/anie.200462884","volume":"44","author":"R Giri","year":"2005","unstructured":"Giri, R., Chen, X. & Yu, J.-Q. Palladium-catalyzed asymmetric iodination of unactivated C-H bonds under mild conditions. Angew. Chem., Int. Ed. 44, 2112\u20132115 (2005).","journal-title":"Angew. Chem., Int. Ed."},{"key":"BFncomms14904_CR20","doi-asserted-by":"crossref","first-page":"13154","DOI":"10.1021\/ja054549f","volume":"127","author":"VG Zaitsev","year":"2005","unstructured":"Zaitsev, V. G. & Daugulis, O. Highly regioselective arylation of sp3 C\u2212H bonds catalyzed by palladium acetate. J. Am. Chem. Soc. 127, 13154\u201313155 (2005).","journal-title":"J. Am. Chem. Soc."},{"key":"BFncomms14904_CR21","doi-asserted-by":"crossref","first-page":"3965","DOI":"10.1021\/ja910900p","volume":"132","author":"D Shabashov","year":"2010","unstructured":"Shabashov, D. & Daugulis, O. Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon\u2212hydrogen bonds. J. Am. Chem. Soc. 132, 3965\u20133972 (2010).","journal-title":"J. Am. Chem. Soc."},{"key":"BFncomms14904_CR22","doi-asserted-by":"crossref","first-page":"2248","DOI":"10.1021\/ol500745t","volume":"16","author":"Y Wei","year":"2014","unstructured":"Wei, Y., Tang, H. & Zeng, X. Pd(II)-catalyzed intermolecular arylation of unactivated C(sp3)\u2013H bonds with aryl bromides enabled by 8-aminoquinoline auxiliary. Org. Lett. 16, 2248\u20132251 (2014).","journal-title":"Org. Lett."},{"key":"BFncomms14904_CR23","doi-asserted-by":"crossref","first-page":"6030","DOI":"10.1021\/ja402806f","volume":"135","author":"R Shang","year":"2013","unstructured":"Shang, R., Ilies, L., Matsumoto, A. & Nakamura, E. \u03b2-arylation of carboxamides via iron-catalyzed C(sp3)\u2013H bond activation. J. Am. Chem. Soc. 135, 6030\u20136032 (2013).","journal-title":"J. Am. Chem. Soc."},{"key":"BFncomms14904_CR24","doi-asserted-by":"crossref","first-page":"697","DOI":"10.1039\/C4OB02389G","volume":"13","author":"G Shan","year":"2015","unstructured":"Shan, G., Huang, G. & Rao, Y. Palladium-catalyzed unactivated \u03b2-methylene C(sp3)\u2013H bond alkenylation of aliphatic amides and its application in a sequential C(sp3)\u2013H\/C(sp2)\u2013H bond alkenylation. Org. Bio. Chem. 13, 697\u2013701 (2015).","journal-title":"Org. Bio. Chem."},{"key":"BFncomms14904_CR25","doi-asserted-by":"crossref","first-page":"11065","DOI":"10.1002\/anie.201406594","volume":"53","author":"BM Monks","year":"2014","unstructured":"Monks, B. M., Fruchey, E. R. & Cook, S. P. Iron-catalyzed C (sp2)H alkylation of carboxamides with primary electrophiles. Angew. Chem., Int. Ed. 53, 11065\u201311069 (2014).","journal-title":"Angew. Chem., Int. Ed."},{"key":"BFncomms14904_CR26","doi-asserted-by":"crossref","first-page":"12135","DOI":"10.1021\/ja406484v","volume":"135","author":"S-Y Zhang","year":"2013","unstructured":"Zhang, S.-Y., Li, Q. & Chen, G. Stereoselective synthesis of \u03b2-alkylated \u03b1-amino acids via palladium-catalyzed alkylation of unactivated methylene C(sp3)\u2013H bonds with primary alkyl halides. J. Am. Chem. Soc. 135, 12135\u201312141 (2013).","journal-title":"J. Am. Chem. Soc."},{"key":"BFncomms14904_CR27","doi-asserted-by":"crossref","first-page":"12984","DOI":"10.1021\/ja206002m","volume":"133","author":"Y Ano","year":"2011","unstructured":"Ano, Y., Tobisu, M. & Chatani, N. Palladium-catalyzed direct ethynylation of C(sp3)\u2013H bonds in aliphatic carboxylic acid derivatives. J. Am. Chem. Soc. 133, 12984\u201312986 (2011).","journal-title":"J. Am. Chem. Soc."},{"key":"BFncomms14904_CR28","doi-asserted-by":"crossref","first-page":"6260","DOI":"10.1021\/ol503248f","volume":"16","author":"B Wang","year":"2014","unstructured":"Wang, B., Lu, C. & Chen, G. Palladium-catalyzed stereoretentive olefination of unactivated C(sp3)\u2013H bonds with vinyl iodides at room temperature: synthesis of \u03b2-vinyl \u03b1-amino acids. Org. Lett. 16, 6260\u20136263 (2014).","journal-title":"Org. Lett."},{"key":"BFncomms14904_CR29","doi-asserted-by":"crossref","first-page":"13606","DOI":"10.1002\/anie.201307090","volume":"52","author":"G Shan","year":"2013","unstructured":"Shan, G., Yang, X. & Rao, Y. An efficient palladium-catalyzed C-H alkoxylation of unactivated methylene and methyl groups with cyclic hypervalent iodine (I3+) oxidants. Angew. Chem., Int. Ed. 52, 13606\u201313610 (2013).","journal-title":"Angew. Chem., Int. Ed."},{"key":"BFncomms14904_CR30","doi-asserted-by":"crossref","first-page":"11124","DOI":"10.1002\/anie.201305615","volume":"52","author":"G He","year":"2013","unstructured":"He, G., Zhang, S.-Y. & Chen, G. Use of a readily removable auxiliary group for the synthesis of pyrrolidones by the palladium-catalyzed intramolecular amination of unactivated \u03b3 C(sp3)-H bonds. Angew. Chem., Int. Ed. 52, 11124\u201311128 (2013).","journal-title":"Angew. Chem., Int. Ed."},{"key":"BFncomms14904_CR31","doi-asserted-by":"crossref","first-page":"4688","DOI":"10.1021\/ol502007t","volume":"16","author":"L Grigorjeva","year":"2014","unstructured":"Grigorjeva, L. & Daugulis, O. Cobalt-catalyzed direct carbonylation of aminoquinoline benzamides. Org. Lett. 16, 4688\u20134690 (2014).","journal-title":"Org. Lett."},{"key":"BFncomms14904_CR32","doi-asserted-by":"crossref","first-page":"1328","DOI":"10.1021\/acs.orglett.5b00337","volume":"17","author":"C Lin","year":"2015","unstructured":"Lin, C., Li, D. & Zhang, Y. Direct ortho-thiolation of arenes and alkenes by nickel catalysis. Org. Lett. 17, 1328\u20131331 (2015).","journal-title":"Org. Lett."},{"key":"BFncomms14904_CR33","doi-asserted-by":"crossref","first-page":"1340","DOI":"10.1021\/acs.orglett.5b00471","volume":"17","author":"C Lin","year":"2015","unstructured":"Lin, C., Yu, W. & Zhang, Y. Nickel-catalyzed direct thioetherification of \u03b2-C(sp3)\u2013H bonds of aliphatic amides. Org. Lett. 17, 1340\u20131343 (2015).","journal-title":"Org. Lett."},{"key":"BFncomms14904_CR34","doi-asserted-by":"crossref","first-page":"3798","DOI":"10.1021\/acs.orglett.5b01774","volume":"17","author":"Q Zhu","year":"2015","unstructured":"Zhu, Q., Ji, D. & Xu, Y. Efficient palladium-catalyzed C\u2013H fluorination of C(sp3)\u2013H bonds: synthesis of \u03b2-fluorinated carboxylic acids. Org. Lett. 17, 3798\u20133801 (2015).","journal-title":"Org. Lett."},{"key":"BFncomms14904_CR35","doi-asserted-by":"crossref","first-page":"12990","DOI":"10.1021\/jacs.5b07424","volume":"137","author":"J Zhang","year":"2015","unstructured":"Zhang, J., Chen, H. & Zhang, Y. Cobalt-catalyzed cyclization of aliphatic amides and terminal alkynes with silver-cocatalyst. J. Am. Chem. Soc. 137, 12990\u201312996 (2015).","journal-title":"J. Am. Chem. Soc."},{"key":"BFncomms14904_CR36","doi-asserted-by":"crossref","first-page":"5188","DOI":"10.1002\/anie.201200731","volume":"51","author":"LD Tran","year":"2012","unstructured":"Tran, L. D. & Daugulis, O. Nonnatural amino acid synthesis by using carbon\u2013hydrogen bond functionalization methodology. Angew. Chem., Int. Ed. 51, 5188\u20135191 (2012).","journal-title":"Angew. Chem., Int. Ed."},{"key":"BFncomms14904_CR37","doi-asserted-by":"crossref","first-page":"13588","DOI":"10.1002\/anie.201306625","volume":"52","author":"Q Zhang","year":"2013","unstructured":"Zhang, Q., Chen, K. & Shi, B.-F. Stereoselective synthesis of chiral \u03b1-amino-\u03b2-lactams through palladium(II)-catalyzed sequential monoarylation\/amidation of C(sp3)-H bonds. Angew. Chem., Int. Ed. 52, 13588\u201313592 (2013).","journal-title":"Angew. Chem., Int. Ed."},{"key":"BFncomms14904_CR38","doi-asserted-by":"crossref","first-page":"7389","DOI":"10.1002\/chem.201406528","volume":"21","author":"K Chen","year":"2015","unstructured":"Chen, K., Li, Z.-W. & Shi, Z.-J. Development of modifiable bidentate amino oxazoline directing group for Pd-catalyzed arylation of secondary C-H bonds. Chem. Eur. J. 21, 7389\u20137393 (2015).","journal-title":"Chem. Eur. J."},{"key":"BFncomms14904_CR39","doi-asserted-by":"crossref","first-page":"4548","DOI":"10.1002\/chem.201304978","volume":"20","author":"LC Misal Castro","year":"2014","unstructured":"Misal Castro, L. C. & Chatani, N. Palladium(II)-catalyzed ortho C-H arylation\/alkylation of N-benzoyl \u03b1-amino ester derivatives. Chem. Eur. J. 20, 4548\u20134553 (2014).","journal-title":"Chem. Eur. J."},{"key":"BFncomms14904_CR40","doi-asserted-by":"crossref","first-page":"16940","DOI":"10.1021\/ja510233h","volume":"136","author":"W Gong","year":"2014","unstructured":"Gong, W., Zhang, G. & Yu, J.-Q. Site-selective C (sp3)\u2013H functionalization of di-, tri-, and tetrapeptides at the N-terminus. J. Am. Chem. Soc. 136, 16940\u201316946 (2014).","journal-title":"J. Am. Chem. Soc."},{"key":"BFncomms14904_CR41","doi-asserted-by":"crossref","first-page":"5966","DOI":"10.1021\/acs.orglett.5b02900","volume":"17","author":"T Toba","year":"2015","unstructured":"Toba, T., Hu, Y. & Yu, J.-Q. \u03b2-C(sp3)\u2013H arylation of \u03b1-hydroxy acid derivatives utilizing amino acid as a directing group. Org. Lett. 17, 5966\u20135969 (2015).","journal-title":"Org. Lett."},{"key":"BFncomms14904_CR42","doi-asserted-by":"crossref","first-page":"3611","DOI":"10.1039\/C5SC01137J","volume":"6","author":"J Kim","year":"2015","unstructured":"Kim, J., Sim, M. & Hong, S. Asymmetric C\u2013H functionalization of cyclopropanes using an isoleucine-NH2 bidentate directing group. Chem. Sci. 6, 3611\u20133616 (2015).","journal-title":"Chem. Sci."},{"key":"BFncomms14904_CR43","doi-asserted-by":"crossref","first-page":"7043","DOI":"10.1039\/C6CC02865A","volume":"52","author":"M Guan","year":"2016","unstructured":"Guan, M., Pang, Y. & Zhao, Y. Pd-catalyzed sequential \u03b2-C(sp3)\u2013H arylation and intramolecular amination of \u03b4-C(sp2)\u2013H bonds for synthesis of quinolinones via an N,O-bidentate directing group. Chem. Comm. 52, 7043\u20137046 (2016).","journal-title":"Chem. Comm."},{"key":"BFncomms14904_CR44","doi-asserted-by":"crossref","first-page":"9886","DOI":"10.1021\/ja903573p","volume":"131","author":"M Wasa","year":"2009","unstructured":"Wasa, M., Engle, K. M. & Yu, J.-Q. Pd(0)\/PR3-catalyzed intermolecular arylation of sp3 C\u2212H bonds. J. Am. Chem. Soc. 131, 9886\u20139887 (2009).","journal-title":"J. Am. Chem. Soc."},{"key":"BFncomms14904_CR45","doi-asserted-by":"crossref","first-page":"19598","DOI":"10.1021\/ja207607s","volume":"133","author":"M Wasa","year":"2011","unstructured":"Wasa, M., Engle, K. M. & Yu, J.-Q. Pd(II)-catalyzed enantioselective C\u2013H activation of cyclopropanes. J. Am. Chem. Soc. 133, 19598\u201319601 (2011).","journal-title":"J. Am. Chem. Soc."},{"key":"BFncomms14904_CR46","doi-asserted-by":"crossref","first-page":"18570","DOI":"10.1021\/ja309325e","volume":"134","author":"M Wasa","year":"2012","unstructured":"Wasa, M., Chan, K. S. L. & Yu, J.-Q. Ligand-enabled methylene C(sp3)\u2013H bond activation with a Pd(II) catalyst. J. Am. Chem. Soc. 134, 18570\u201318572 (2012).","journal-title":"J. Am. Chem. Soc."},{"key":"BFncomms14904_CR47","doi-asserted-by":"crossref","first-page":"1216","DOI":"10.1126\/science.1249198","volume":"343","author":"J He","year":"2014","unstructured":"He, J., Li, S. & Yu, J.-Q. Ligand-controlled C (sp3)\u2013H arylation and olefination in synthesis of unnatural chiral \u03b1\u2013amino acids. Science 343, 1216\u20131220 (2014).","journal-title":"Science"},{"key":"BFncomms14904_CR48","doi-asserted-by":"crossref","first-page":"7190","DOI":"10.1021\/ja801355s","volume":"130","author":"D-H Wang","year":"2008","unstructured":"Wang, D.-H., Wasa, M. & Yu, J.-Q. Pd(II)-catalyzed cross-coupling of sp3 C\u2212H bonds with sp2 and sp3 boronic acids using air as the oxidant. J. Am. Chem. Soc. 130, 7190\u20137191 (2008).","journal-title":"J. Am. Chem. Soc."},{"key":"BFncomms14904_CR49","doi-asserted-by":"crossref","first-page":"3338","DOI":"10.1021\/ja512690x","volume":"137","author":"G Chen","year":"2015","unstructured":"Chen, G., Shigenari, T. & Yu, J.-Q. Ligand-enabled \u03b2-C\u2013H arylation of \u03b1-amino acids using a simple and practical auxiliary. J. Am. Chem. Soc. 137, 3338\u20133351 (2015).","journal-title":"J. Am. Chem. Soc."},{"key":"BFncomms14904_CR50","doi-asserted-by":"crossref","first-page":"911","DOI":"10.1021\/ar200318q","volume":"45","author":"JL Roizen","year":"2012","unstructured":"Roizen, J. L., Harvey, M. E. & Du Bois, J. Metal-catalyzed nitrogen-atom transfer methods for the oxidation of aliphatic C\u2013H bonds. Acc. Chem. Res. 45, 911\u2013922 (2012).","journal-title":"Acc. Chem. Res."},{"key":"BFncomms14904_CR51","doi-asserted-by":"crossref","first-page":"1855","DOI":"10.1039\/c1cs90010b","volume":"40","author":"HML Davies","year":"2011","unstructured":"Davies, H. M. L., Du Bois, J. & Yu, J.-Q. Recent advances in the transition metal-catalyzed twofold oxidative C\u2013H bond activation strategy for C\u2013C and C\u2013N bond formation. Chem. Soc. Rev. 40, 1855\u20131856 (2011).","journal-title":"Chem. Soc. Rev."},{"key":"BFncomms14904_CR52","doi-asserted-by":"crossref","first-page":"1074","DOI":"10.1021\/ar9000058","volume":"42","author":"O Daugulis","year":"2009","unstructured":"Daugulis, O., Do, H.-Q. & Shabashov, D. Palladium- and copper-catalyzed arylation of carbon\u2212hydrogen bonds. Acc. Chem. Res. 42, 1074\u20131086 (2009).","journal-title":"Acc. Chem. Res."},{"key":"BFncomms14904_CR53","doi-asserted-by":"crossref","first-page":"635","DOI":"10.1021\/acs.accounts.6b00022","volume":"49","author":"G He","year":"2016","unstructured":"He, G., Wang, B., Nack, W. A. & Chen, G. Syntheses and transformations of \u03b1-amino acids via palladium-catalyzed auxiliary-directed sp3 C\u2013H functionalization. Acc. Chem. Res. 49, 635\u2013645 (2016).","journal-title":"Acc. Chem. Res."},{"key":"BFncomms14904_CR54","doi-asserted-by":"crossref","first-page":"3952","DOI":"10.1039\/C4SC01545B","volume":"5","author":"B Wang","year":"2014","unstructured":"Wang, B., Nack, W. A. & Chen, G. Palladium-catalyzed trifluoroacetate-promoted mono-arylation of the \u03b2-methyl group of alanine at room temperature: synthesis of \u03b2-arylated \u03b1-amino acids through sequential C\u2013H functionalization. Chem. Sci. 5, 3952\u20133957 (2014).","journal-title":"Chem. Sci."},{"key":"BFncomms14904_CR55","doi-asserted-by":"crossref","first-page":"1023","DOI":"10.1126\/science.aaf4434","volume":"353","author":"G Chen","year":"2016","unstructured":"Chen, G., Gong, W. & Yu, J.-Q. Ligand-accelerated enantioselective methylene C(sp3)-H bond activation. Science 353, 1023\u20131027 (2016).","journal-title":"Science"},{"key":"BFncomms14904_CR56","doi-asserted-by":"crossref","first-page":"140","DOI":"10.1038\/nchem.2619","volume":"9","author":"P Jain","year":"2017","unstructured":"Jain, P., Verma, P., Xia, G. & Yu, J.-Q. Enantioselective amine \u03b1-functionalization via palladium-catalysed C-H arylation of thioamides. Nat. Chem. 9, 140\u2013144 (2017).","journal-title":"Nat. Chem."},{"key":"BFncomms14904_CR57","doi-asserted-by":"crossref","first-page":"4882","DOI":"10.1002\/anie.200801030","volume":"47","author":"B-F Shi","year":"2008","unstructured":"Shi, B.-F., Maugel, N. & Yu, J.-Q. PdII-catalyzed enantioselective activation of C(sp2)-H and C(sp3)-H bonds using monoprotected amino acids as chiral ligands. Angew. Chem., Int. Ed. 47, 4882\u20134886 (2008).","journal-title":"Angew. Chem., Int. Ed."},{"key":"BFncomms14904_CR58","doi-asserted-by":"crossref","first-page":"14137","DOI":"10.1021\/ja105044s","volume":"132","author":"KM Engle","year":"2010","unstructured":"Engle, K. M., Wang, D.-H. & Yu, J.-Q. Ligand-accelerated C\u2212H activation reactions: evidence for a switch of mechanism. J. Am. Chem. Soc. 132, 14137\u201314151 (2010).","journal-title":"J. Am. Chem. Soc."},{"key":"BFncomms14904_CR59","doi-asserted-by":"crossref","first-page":"1690","DOI":"10.1021\/ja208661v","volume":"134","author":"DG Musaev","year":"2012","unstructured":"Musaev, D. G., Kaledin, A. & Yu, J.-Q. Key mechanistic features of enantioselective C\u2013H bond activation reactions catalyzed by [(chiral mono-N-protected amino acid)\u2013Pd(II)] complexes. J. Am. Chem. Soc. 134, 1690\u20131698 (2012).","journal-title":"J. Am. Chem. Soc."},{"key":"BFncomms14904_CR60","doi-asserted-by":"crossref","first-page":"14118","DOI":"10.1021\/ja304643e","volume":"134","author":"R Giri","year":"2012","unstructured":"Giri, R., Lan, Y. & Yu, J.-Q. Understanding reactivity and stereoselectivity in palladium-catalyzed diastereoselective sp3 C\u2013H bond activation: intermediate characterization and computational studies. J. Am. Chem. Soc. 134, 14118\u201314126 (2012).","journal-title":"J. Am. Chem. Soc."},{"key":"BFncomms14904_CR61","doi-asserted-by":"crossref","first-page":"894","DOI":"10.1021\/ja411683n","volume":"136","author":"G-J Cheng","year":"2014","unstructured":"Cheng, G.-J., Yang, Y.-F., Yu, J.-Q. & Wu, Y.-D. Role of N-Acyl amino acid ligands in Pd(II)-catalyzed remote C\u2013H activation of tethered arenes. J. Am. Chem. Soc. 136, 894\u2013897 (2014).","journal-title":"J. Am. Chem. Soc."},{"key":"BFncomms14904_CR62","doi-asserted-by":"crossref","first-page":"16346","DOI":"10.1021\/ja907150m","volume":"131","author":"JM Chalker","year":"2009","unstructured":"Chalker, J. M., Wood, C. S. C. & Davis, B. G. A convenient catalyst for aqueous and protein Suzuki\u2212Miyaura cross-coupling. J. Am. Chem. Soc. 131, 16346\u201316347 (2009).","journal-title":"J. Am. Chem. Soc."},{"key":"BFncomms14904_CR63","doi-asserted-by":"crossref","first-page":"4477","DOI":"10.1039\/C5CC00476D","volume":"51","author":"L Han","year":"2015","unstructured":"Han, L., Zhang, Y. & Wang, Y. Assembly of twisted luminescent architectures based on acenaphtho[1,2-k]fluoranthene derivatives. Chem. Comm. 51, 4477\u20134480 (2015).","journal-title":"Chem. Comm."},{"key":"BFncomms14904_CR64","doi-asserted-by":"crossref","first-page":"6965","DOI":"10.1016\/S0040-4039(97)01665-1","volume":"38","author":"GM Salamonczyk","year":"1997","unstructured":"Salamonczyk, G. M., Oza, V. B. & Sih, C. J. A concise synthesis of thyroxine (T4) and 3,5,3\u2032-Triiodo-l-thyronine (T3). Tet. Let. 38, 6965\u20136968 (1997).","journal-title":"Tet. Let."},{"key":"BFncomms14904_CR65","doi-asserted-by":"crossref","first-page":"1021","DOI":"10.1016\/S0957-4166(00)86152-2","volume":"2","author":"M Colombo","year":"1991","unstructured":"Colombo, M., De Amici, M., De Micheli, C., Pitr\u00e9, D., Carrea, G. & Riva, S. Chemoenzymatic synthesis of the enantiomers of iopanoic acid. Tetrahedron 2, 1021\u20131030 (1991).","journal-title":"Tetrahedron"},{"key":"BFncomms14904_CR66","doi-asserted-by":"crossref","first-page":"11180","DOI":"10.1002\/chem.201501123","volume":"21","author":"G-J Cheng","year":"2015","unstructured":"Cheng, G.-J., Chen, P. & Wu, Y.-D. A combined IM-MS\/DFT study on [Pd(MPAA)]-catalyzed enantioselective CH activation: relay of chirality through a rigid framework. Chem. Eur. J. 21, 11180\u201311188 (2015).","journal-title":"Chem. Eur. J."},{"key":"BFncomms14904_CR67","doi-asserted-by":"crossref","first-page":"457","DOI":"10.1111\/j.1399-3011.1994.tb00182.x","volume":"44","author":"MH Kim","year":"1994","unstructured":"Kim, M. H., Lai, J. H. & Hangauer, D. G. Tetrapeptide tyrosine kinase inhibitors. Enantioselective synthesis of p-hydroxymethyl-L-phenylalanine, incorporation into a tetrapeptide, and subsequent elaboration into p-(R,S-hydroxyphosphonomethyl)-L-phenylalanine. Int. J. Pept. Prot. Res. 44, 457\u2013465 (1994).","journal-title":"Int. J. Pept. Prot. Res."}],"container-title":["Nature Communications"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.nature.com\/articles\/ncomms14904.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.nature.com\/articles\/ncomms14904","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/www.nature.com\/doifinder\/10.1038\/ncomms14904","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"},{"URL":"https:\/\/www.nature.com\/articles\/ncomms14904.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,12,23]],"date-time":"2022-12-23T00:24:01Z","timestamp":1671755041000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.nature.com\/articles\/ncomms14904"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,4,6]]},"references-count":67,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2017,4,28]]}},"alternative-id":["BFncomms14904"],"URL":"https:\/\/doi.org\/10.1038\/ncomms14904","relation":{},"ISSN":["2041-1723"],"issn-type":[{"value":"2041-1723","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,4,6]]},"assertion":[{"value":"21 November 2016","order":1,"name":"received","label":"Received","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"10 February 2017","order":2,"name":"accepted","label":"Accepted","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"6 April 2017","order":3,"name":"first_online","label":"First Online","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"The authors declare no competing financial interests.","order":1,"name":"Ethics","group":{"name":"EthicsHeading","label":"Competing interests"}}],"article-number":"14904"}}