{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,17]],"date-time":"2026-09-17T00:00:54Z","timestamp":1789603254006,"version":"build-2803163510"},"reference-count":116,"publisher":"Wiley","issue":"51","license":[{"start":{"date-parts":[[2021,11,16]],"date-time":"2021-11-16T00:00:00Z","timestamp":1637020800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["21831002"],"award-info":[{"award-number":["21831002"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005153","name":"China National Funds for Distinguished Young Scientists","doi-asserted-by":"publisher","award":["22025103"],"award-info":[{"award-number":["22025103"]}],"id":[{"id":"10.13039\/501100005153","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2021,12,13]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The intermolecular asymmetric radical oxidative C(sp<jats:sup>3<\/jats:sup>)\u2212C(sp) cross\u2010coupling of C(sp<jats:sup>3<\/jats:sup>)\u2212H bonds with readily available terminal alkynes is a promising method to forge chiral C(sp<jats:sup>3<\/jats:sup>)\u2212C(sp) bonds because of the high atom and step economy, but remains underexplored. Here, we report a copper\u2010catalyzed asymmetric C(sp<jats:sup>3<\/jats:sup>)\u2212C(sp) cross\u2010coupling of (hetero)benzylic and (cyclic)allylic C\u2212H bonds with terminal alkynes that occurs with high to excellent enantioselectivity. Critical to the success is the rational design of chiral oxazoline\u2010derived N,N,P(O)\u2010ligands that not only tolerate the strong oxidative conditions which are requisite for intermolecular hydrogen atom abstraction (HAA) processes but also induce the challenging enantiocontrol. Direct access to a range of synthetically useful chiral benzylic alkynes and 1,4\u2010enynes, high site\u2010selectivity among similar C(sp<jats:sup>3<\/jats:sup>)\u2212H bonds, and facile synthesis of enantioenriched medicinally relevant compounds make this approach very attractive.<\/jats:p>","DOI":"10.1002\/anie.202110233","type":"journal-article","created":{"date-parts":[[2021,10,5]],"date-time":"2021-10-05T22:55:42Z","timestamp":1633474542000},"page":"26710-26717","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":74,"title":["Copper\u2010Catalyzed Intermolecular Enantioselective Radical Oxidative C(sp<sup>3<\/sup>)\u2212H\/C(sp)\u2212H Cross\u2010Coupling with Rationally Designed Oxazoline\u2010Derived N,N,P(O)\u2010Ligands"],"prefix":"10.1002","volume":"60","author":[{"given":"Lin","family":"Liu","sequence":"first","affiliation":[{"name":"Shenzhen Grubbs Institute and Department of Chemistry Guangdong Provincial Key Laboratory of Catalysis Southern University of Science and Technology  Shenzhen 518055 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kai\u2010Xin","family":"Guo","sequence":"additional","affiliation":[{"name":"Shenzhen Grubbs Institute and Department of Chemistry Guangdong Provincial Key Laboratory of Catalysis Southern University of Science and Technology  Shenzhen 518055 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yu","family":"Tian","sequence":"additional","affiliation":[{"name":"Shenzhen Grubbs Institute and Department of Chemistry Guangdong Provincial Key Laboratory of Catalysis Southern University of Science and Technology  Shenzhen 518055 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chang\u2010Jiang","family":"Yang","sequence":"additional","affiliation":[{"name":"Shenzhen Grubbs Institute and Department of Chemistry Guangdong Provincial Key Laboratory of Catalysis Southern University of Science and Technology  Shenzhen 518055 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qiang\u2010Shuai","family":"Gu","sequence":"additional","affiliation":[{"name":"Academy for Advanced Interdisciplinary Studies and Department of Chemistry Southern University of Science and Technology  Shenzhen 518055 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhong\u2010Liang","family":"Li","sequence":"additional","affiliation":[{"name":"Academy for Advanced Interdisciplinary Studies and Department of Chemistry Southern University of Science and Technology  Shenzhen 518055 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Liu","family":"Ye","sequence":"additional","affiliation":[{"name":"Academy for Advanced Interdisciplinary Studies and Department of Chemistry Southern University of Science and Technology  Shenzhen 518055 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6978-6465","authenticated-orcid":false,"given":"Xin\u2010Yuan","family":"Liu","sequence":"additional","affiliation":[{"name":"Shenzhen Grubbs Institute and Department of Chemistry Guangdong Provincial Key Laboratory of Catalysis Southern University of Science and Technology  Shenzhen 518055 China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,11,16]]},"reference":[{"key":"e_1_2_6_1_1","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","volume-title":"Acetylene Chemistry: Chemistry, Biology, and Material Science","author":"Diederich F.","year":"2005"},{"key":"e_1_2_6_3_2","volume-title":"Modern Alkyne Chemistry: Catalytic and Atom-Economic Transformations","author":"Trost B. M.","year":"2015"},{"key":"e_1_2_6_4_1","unstructured":"\u00a0"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aal5175"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aao4798"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b01124"},{"key":"e_1_2_6_8_1","unstructured":"For terminal alkynes as nucleophiles 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representative examples for the synthesis of chiral 1 4-enynes from terminal alkynes see"},{"key":"e_1_2_6_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja5084333"},{"key":"e_1_2_6_67_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201300785"},{"key":"e_1_2_6_67_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201300785"},{"key":"e_1_2_6_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b12806"},{"key":"e_1_2_6_69_1","unstructured":"For racemic example see"},{"key":"e_1_2_6_70_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201801772"},{"key":"e_1_2_6_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b05668"},{"key":"e_1_2_6_72_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201603576"},{"key":"e_1_2_6_72_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201603576"},{"key":"e_1_2_6_73_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2010.08.051"},{"key":"e_1_2_6_74_1","unstructured":"For selected reviews see"},{"key":"e_1_2_6_75_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0cs00217h"},{"key":"e_1_2_6_76_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0cs00142b"},{"key":"e_1_2_6_77_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-018-0020-0"},{"key":"e_1_2_6_78_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature24641"},{"key":"e_1_2_6_79_1","unstructured":"\u00a0"},{"key":"e_1_2_6_80_2","doi-asserted-by":"publisher","DOI":"10.2533\/chimia.2020.23"},{"key":"e_1_2_6_81_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2020.07.007"},{"key":"e_1_2_6_82_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.9b00916"},{"key":"e_1_2_6_83_1","unstructured":"For some examples of HAA-initiated functionalization of C(sp3)\u2212H bonds using excessive C\u2212H substrates see"},{"key":"e_1_2_6_84_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-020-2831-6"},{"key":"e_1_2_6_85_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41929-019-0357-9"},{"key":"e_1_2_6_86_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c10471"},{"key":"e_1_2_6_87_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-019-11392-6"},{"key":"e_1_2_6_88_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c01556"},{"key":"e_1_2_6_89_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-019-09857-9"},{"key":"e_1_2_6_90_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-020-0436-1"},{"key":"e_1_2_6_91_1","unstructured":"\u00a0"},{"key":"e_1_2_6_92_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja054506z"},{"key":"e_1_2_6_93_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja8049996"},{"key":"e_1_2_6_94_1","unstructured":"\u00a0"},{"key":"e_1_2_6_95_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201000344"},{"key":"e_1_2_6_96_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00069a040"},{"key":"e_1_2_6_97_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c03304"},{"key":"e_1_2_6_98_1","unstructured":"\u00a0"},{"key":"e_1_2_6_99_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar50082a006"},{"key":"e_1_2_6_100_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar9501434"},{"key":"e_1_2_6_101_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2009.09.025"},{"key":"e_1_2_6_102_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja410756b"}],"container-title":["Angewandte 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