{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,20]],"date-time":"2026-10-20T12:41:38Z","timestamp":1792500098918,"version":"4.5.0"},"reference-count":115,"publisher":"American Chemical Society (ACS)","issue":"20","license":[{"start":{"date-parts":[[2026,10,9]],"date-time":"2026-10-09T00:00:00Z","timestamp":1791504000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,10,9]],"date-time":"2026-10-09T00:00:00Z","timestamp":1791504000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,10,9]],"date-time":"2026-10-09T00:00:00Z","timestamp":1791504000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/100011769","name":"Scripps Research","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100011769","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100002491","name":"Bristol-Myers Squibb","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100002491","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"publisher","award":["2R01 GM084019"],"award-info":[{"award-number":["2R01 GM084019"]}],"id":[{"id":"10.13039\/100000057","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"publisher","award":["R35 GM158311"],"award-info":[{"award-number":["R35 GM158311"]}],"id":[{"id":"10.13039\/100000057","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,20]]},"abstract":"<jats:title>Conspectus<\/jats:title>\n                  <jats:p>In the past two decades, transition metal-catalyzed C\u2013H activation has emerged as an attractive and valuable strategy for enabling novel disconnections in the synthesis of natural products and pharmaceuticals. Substrate-directed C\u2013H activation, which employs pre-coordination of a substrate\u2019s functional group with the catalyst to recruit it for C\u2013H metalation with high site-selectivity, is a particularly powerful approach. Early directed C\u2013H activations relied on bespoke directing groups with separate installation and removal steps, reducing synthetic efficiency and practicality (limited functional group tolerance, substrate scope). The development of C\u2013H activation methods which use functional groups native to common building blocks and synthetic intermediates would be highly valuable.<\/jats:p>\n                  <jats:p>In this account, we highlight the discovery and development of a transient directing group (TDG) platform for Pd-catalyzed C\u2013H activation reactions of native aldehydes, ketones, and amines. This approach leverages the reversible imine formation event between the substrate and a complementary TDG motif to transiently generate the optimal L,X-type assembly capable of recruiting Pd catalysts for a diverse range of C\u2013H activation reactions, including C\u2013C, C\u2013halogen, C\u2013O, and C\u2013N bond formations. We also describe the application of pyridone ligands in concert with the TDG approach to amplify the reactivity of the Pd catalysts and to activate previously inaccessible C\u2013H bonds. Finally, we cover notable applications of Pd-catalyzed TDG C\u2013H activation in complex molecule synthesis.<\/jats:p>","DOI":"10.1021\/acs.accounts.6c00521","type":"journal-article","created":{"date-parts":[[2026,10,9]],"date-time":"2026-10-09T17:02:05Z","timestamp":1791565325000},"page":"3481-3499","source":"Crossref","is-referenced-by-count":0,"title":["Transient Directing\nGroups for Enhancing Affinity\nbetween Native Substrates and Transition Metal C\u2013H Activation\nCatalysts"],"prefix":"10.1021","volume":"59","author":[{"ORCID":"https:\/\/orcid.org\/0009-0008-7649-842X","authenticated-orcid":true,"given":"Jordan R.","family":"Yirak","sequence":"first","affiliation":[{"name":"The Scripps Research Institute , , 10550 N. Torrey Pines Rd. , , ,","place":["La Jolla, California, United States, 92037"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8125-8019","authenticated-orcid":true,"given":"Zhen","family":"Wang","sequence":"additional","affiliation":[{"name":"The Scripps Research Institute , , 10550 N. Torrey Pines Rd. , , ,","place":["La Jolla, California, United States, 92037"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0285-9663","authenticated-orcid":true,"given":"Martin","family":"Tomanik","sequence":"additional","affiliation":[{"name":"The Scripps Research Institute , , 10550 N. Torrey Pines Rd. , , ,","place":["La Jolla, California, United States, 92037"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5379-4172","authenticated-orcid":true,"given":"Yan-Qiao","family":"Chen","sequence":"additional","affiliation":[{"name":"The Scripps Research Institute , , 10550 N. Torrey Pines Rd. , , ,","place":["La Jolla, California, United States, 92037"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kevin","family":"Wu","sequence":"additional","affiliation":[{"name":"The Scripps Research Institute , , 10550 N. Torrey Pines Rd. , , ,","place":["La Jolla, California, United States, 92037"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3560-5774","authenticated-orcid":true,"given":"Jin-Quan","family":"Yu","sequence":"additional","affiliation":[{"name":"The Scripps Research Institute , , 10550 N. Torrey Pines Rd. , , ,","place":["La Jolla, California, United States, 92037"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,10,9]]},"reference":[{"key":"2026102007261447000_cit1","doi-asserted-by":"publisher","first-page":"252","DOI":"10.1126\/science.aad7893","article-title":"Functionalization\nof C(sp3)\u2013H bonds using a transient directing group","volume":"351","author":"Zhang","year":"2016","journal-title":"Science"},{"key":"2026102007261447000_cit2","doi-asserted-by":"publisher","first-page":"14554","DOI":"10.1021\/jacs.6b09653","article-title":"Pd-Catalyzed\n\u03b3-C(sp3)\u2013H Arylation of Free Amines Using\na Transient Directing Group","volume":"138","author":"Wu","year":"2016","journal-title":"J. Am. Chem. Soc."},{"key":"2026102007261447000_cit3","doi-asserted-by":"publisher","first-page":"17884","DOI":"10.1021\/jacs.8b07109","article-title":"Overcoming\nthe Limitations of \u03b3- and \u03b4-C\u2013H Arylation of Amines\nthrough Ligand Development","volume":"140","author":"Chen","year":"2018","journal-title":"J. Am. Chem. Soc."},{"key":"2026102007261447000_cit4a","doi-asserted-by":"publisher","first-page":"5094","DOI":"10.1002\/anie.200806273","article-title":"Palladium(II)-Catalyzed\nC\u2013H Activation\/C\u2013C Cross-Coupling Reactions: Versatility\nand Practicality","volume":"48","author":"Chen","year":"2009","journal-title":"Angew. Chem. Int. Ed."},{"key":"2026102007261447000_cit4b","doi-asserted-by":"publisher","first-page":"788","DOI":"10.1021\/ar200185g","article-title":"Weak Coordination\nas a Powerful Means for Developing Broadly Useful C\u2013H Functionalization\nReactions","volume":"45","author":"Engle","year":"2012","journal-title":"Acc. Chem. Res."},{"key":"2026102007261447000_cit4c","doi-asserted-by":"publisher","first-page":"1147","DOI":"10.1021\/cr900184e","article-title":"Palladium-Catalyzed Ligand-Directed\nC\u2013H Functionalization Reactions","volume":"110","author":"Lyons","year":"2010","journal-title":"Chem.\nRev."},{"key":"2026102007261447000_cit4d","doi-asserted-by":"publisher","first-page":"1053","DOI":"10.1021\/ar5004626","article-title":"Bidentate,\nMonoanionic Auxiliary-Directed Functionalization of Carbon\u2013Hydrogen\nBonds","volume":"48","author":"Daugulis","year":"2015","journal-title":"Acc. Chem. Res."},{"key":"2026102007261447000_cit4e","doi-asserted-by":"publisher","first-page":"3965","DOI":"10.1021\/ja910900p","article-title":"Auxiliary-Assisted Palladium-Catalyzed\nArylation and Alkylation of sp2 and sp3 Carbon\u2013Hydrogen\nBonds","volume":"132","author":"Shabashov","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"2026102007261447000_cit4f","doi-asserted-by":"publisher","first-page":"14957","DOI":"10.1021\/acs.chemrev.1c00519","article-title":"Transition-Metal-Catalyzed, Coordination-Assisted Functionalization\nof Nonactivated C(sp3)\u2013H Bonds","volume":"121","author":"Liu","year":"2021","journal-title":"Chem. Rev."},{"key":"2026102007261447000_cit5","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202400509","article-title":"Palladium (II)-Catalyzed C\u2013H\nActivation with Bifunctional Ligands: From Curiosity to Industrialization","volume":"63","author":"Wu","year":"2024","journal-title":"Angew. Chem. Int. Ed."},{"key":"2026102007261447000_cit6","doi-asserted-by":"publisher","first-page":"8927","DOI":"10.1021\/jo400159y","article-title":"Developing Ligands for Palladium(II)-Catalyzed C\u2013H Functionalization:\nIntimate Dialogue between Ligand and Substrate","volume":"78","author":"Engle","year":"2013","journal-title":"J. Org. Chem."},{"key":"2026102007261447000_cit7a","doi-asserted-by":"publisher","first-page":"4582","DOI":"10.1039\/C8OB00926K","article-title":"Transient imines\nas \u2018next generation\u2019 directing groups for the catalytic\nfunctionalisation of C\u2013H bonds in a single operation","volume":"16","author":"St John-Campbell","year":"2018","journal-title":"Org. Biomol. Chem."},{"key":"2026102007261447000_cit7b","doi-asserted-by":"publisher","first-page":"7291","DOI":"10.1039\/D0OB01587C","article-title":"Transient imine directing groups for the C\u2013H\nfunctionalisation of aldehydes, ketones and amines: an update 2018\u20132020","volume":"18","author":"Higham","year":"2020","journal-title":"Org. Biomol. Chem."},{"key":"2026102007261447000_cit7c","doi-asserted-by":"publisher","first-page":"12898","DOI":"10.1021\/acscatal.0c03317","article-title":"Chiral Transient Directing Groups\nin Transition-Metal-Catalyzed Enantioselective C\u2013H Bond Functionalization","volume":"10","author":"Lapuh","year":"2020","journal-title":"ACS Catal."},{"key":"2026102007261447000_cit7d","doi-asserted-by":"publisher","first-page":"19773","DOI":"10.1002\/anie.202008437","article-title":"Transition Metal-Catalyzed\nEnantioselective C\u2013H Functionalization via Chiral Transient\nDirecting Group Strategies","volume":"59","author":"Liao","year":"2020","journal-title":"Angew. Chem. Int.\nEd."},{"key":"2026102007261447000_cit8","unstructured":"As of June\n26, 2026 from Web of Science (https:\/\/www.webofscience.com\/wos\/woscc\/smart-search) from the top 5 TDG publications from our group."},{"key":"2026102007261447000_cit9a","doi-asserted-by":"publisher","first-page":"1352","DOI":"10.1002\/(SICI)1521-3773(20000417)39:8&lt;1352::AID-ANIE1352&gt;3.0.CO;2-J","article-title":"The Catalytic Asymmetric\nAldol Reaction","volume":"39","author":"Machajewski","year":"2000","journal-title":"Angew. Chem. Int. 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Soc."},{"key":"2026102007261447000_cit18","doi-asserted-by":"publisher","first-page":"1200","DOI":"10.1021\/jo961887d","article-title":"Chelation-Assisted Intermolecular Hydroacylation: Direct\nSynthesis of Ketone from Aldehyde and 1-Alkene","volume":"62","author":"Jun","year":"1997","journal-title":"J. Org. Chem."},{"key":"2026102007261447000_cit19","doi-asserted-by":"publisher","first-page":"485","DOI":"10.1002\/1521-3765(20020118)8:2&lt;485::AID-CHEM485&gt;3.0.CO;2-1","article-title":"Chelation-Assisted RhI-Catalyzed ortho-Alkylation of\nAromatic Ketimines or Ketones with Olefins","volume":"8","author":"Jun","year":"2002","journal-title":"Chem. Eur. J."},{"key":"2026102007261447000_cit20","doi-asserted-by":"publisher","first-page":"68","DOI":"10.1126\/science.1254465","article-title":"Regioselective ketone\n\u03b1-alkylation with simple olefins via\ndual activation","volume":"345","author":"Mo","year":"2014","journal-title":"Science"},{"key":"2026102007261447000_cit21a","doi-asserted-by":"publisher","first-page":"12015","DOI":"10.1021\/jacs.0c04801","article-title":"Pd(II)-Catalyzed\nEnantioselective \u03b3-C(sp3)\u2013H Functionalizations\nof Free Cyclopropylmethylamines","volume":"142","author":"Zhuang","year":"2020","journal-title":"J. Am. 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Lett."},{"key":"2026102007261447000_cit28","doi-asserted-by":"publisher","first-page":"7523","DOI":"10.1002\/anie.200802651","article-title":"Hydrolytic Stability\nof Hydrazones and Oximes","volume":"47","author":"Kalia","year":"2008","journal-title":"Angew. Chem. Int.\nEd."},{"key":"2026102007261447000_cit29","unstructured":"A few examples of C\u2013H\nactivation with Pd using pre-formed imine assemblies have been reported,\nsee ref 30."},{"key":"2026102007261447000_cit30a","doi-asserted-by":"publisher","first-page":"11856","DOI":"10.1021\/ja027311p","article-title":"C\u2013C Bond Formation via C\u2013H\nBond Activation: Synthesis of the Core of Teleocidin B4","volume":"124","author":"Dangel","year":"2002","journal-title":"J. Am. Chem. 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