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The major challenge arises from the easy generation of a P\u2010centered radical from the P\u2212H\u2010type reagent and its facile addition to the terminal side of alkenes, leading to reverse chemoselectivity. We herein disclose a radical 1,2\u2010carbophosphonylation of styrenes in a highly chemo\u2010 and enantioselective manner. The key to the success lies in not only the implementation of dialkyl phosphites with a strong bond dissociation energy to promote the desired chemoselectivity but also the utilization of an anionic chiral <jats:italic>N,N,N<\/jats:italic>\u2010ligand to forge the chiral C(sp<jats:sup>3<\/jats:sup>)\u2212P bond. The developed Cu\/<jats:italic>N,N,N<\/jats:italic>\u2010ligand catalyst has enriched our library of single\u2010electron transfer catalysts in the enantioselective radical transformations.<\/jats:p>","DOI":"10.1002\/anie.202218523","type":"journal-article","created":{"date-parts":[[2023,2,1]],"date-time":"2023-02-01T13:46:02Z","timestamp":1675259162000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":39,"title":["Copper\u2010Catalyzed Chemo\u2010 and Enantioselective Radical 1,2\u2010Carbophosphonylation of Styrenes"],"prefix":"10.1002","volume":"62","author":[{"given":"Huan","family":"Zhou","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":"Li\u2010Wen","family":"Fan","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":"Yang\u2010Qing","family":"Ren","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":"Li\u2010Lei","family":"Wang","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"},{"name":"School of Science and Institute of Scientific Research Great Bay University  Dongguan 523000 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"}]},{"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":[[2023,2,16]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"For reviews on well-established asymmetric dihydroxylation and epoxidation of alkenes see:"},{"key":"e_1_2_7_2_2","first-page":"159","volume-title":"Asymmetric Catalytic Epoxidation of Unfunctionalized Olefins in Catalytic Asymmetric Synthesis","author":"Jacobsen E. 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see:"},{"key":"e_1_2_7_64_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.9b00381"},{"key":"e_1_2_7_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c06718"},{"key":"e_1_2_7_66_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-019-0346-2"},{"key":"e_1_2_7_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c09125"},{"key":"e_1_2_7_68_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202009527"},{"key":"e_1_2_7_68_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202009527"},{"key":"e_1_2_7_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c07726"},{"key":"e_1_2_7_70_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-022-00954-9"},{"key":"e_1_2_7_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c00957"},{"key":"e_1_2_7_72_1","unstructured":"For selected reviews 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Synth."},{"key":"e_1_2_7_88_2","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.201600512"},{"key":"e_1_2_7_89_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja408031s"},{"key":"e_1_2_7_90_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-019-11528-8"},{"key":"e_1_2_7_91_2","doi-asserted-by":"publisher","DOI":"10.31635\/ccschem.021.202101615"},{"key":"e_1_2_7_92_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2006.02.049"},{"key":"e_1_2_7_93_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja110534g"},{"key":"e_1_2_7_94_1","unstructured":"\u00a0"},{"key":"e_1_2_7_95_2","doi-asserted-by":"publisher","DOI":"10.1139\/v05-163"},{"key":"e_1_2_7_96_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2017.03.021"},{"key":"e_1_2_7_97_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-018-06240-y"},{"key":"e_1_2_7_98_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.1c00212"},{"key":"e_1_2_7_99_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-020-14459-x"},{"key":"e_1_2_7_100_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-022-28285-w"},{"key":"e_1_2_7_101_1","unstructured":"The X-ray analysis of Cu\/N N N-ligand showed a close-to-planar geometry suggesting that it may be less sterically crowded than the Cu\/N N P-ligand system. For rough comparison see Scheme\u2005 and ref.\u2005[5f]."},{"key":"e_1_2_7_102_1","unstructured":"The reaction time could be shortened to less than 3\u2005days by starting the reaction at \u22125\u2009\u00b0C and allowing it to react at rt. See Table\u2005S1 (entry\u200517) for details."},{"key":"e_1_2_7_103_1","unstructured":"\u00a0"},{"key":"e_1_2_7_104_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2015.04.117"},{"key":"e_1_2_7_105_2","doi-asserted-by":"publisher","DOI":"10.1039\/C2DT31971C"},{"key":"e_1_2_7_106_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11164-021-04433-7"},{"key":"e_1_2_7_107_1","unstructured":"The hydrophosphinoylation may also be formed via the addition of Cu\u2212P species to alkenes see:"},{"key":"e_1_2_7_108_2","doi-asserted-by":"publisher","DOI":"10.6023\/cjoc201602018"},{"key":"e_1_2_7_109_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CC06570F"},{"key":"e_1_2_7_110_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2010.09.069"},{"key":"e_1_2_7_111_1","unstructured":"Deposition numbers\u20052219839 2219840 and 2219841contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum KarlsruheAccess Structures service."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202218523","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202218523","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202218523","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,21]],"date-time":"2023-08-21T22:55:21Z","timestamp":1692658521000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202218523"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,2,16]]},"references-count":118,"journal-issue":{"issue":"13","published-print":{"date-parts":[[2023,3,20]]}},"alternative-id":["10.1002\/anie.202218523"],"URL":"https:\/\/doi.org\/10.1002\/anie.202218523","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,2,16]]},"assertion":[{"value":"2022-12-14","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-02-16","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202218523"}}