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While organoboron species are commonly employed as nucleophiles in cross\u2010coupling reactions, their potential as racemic building blocks in enantioconvergent transformations remains largely untapped. Herein, we demonstrate the direct utilization of alkylboronic pinacol esters in intermolecular enantioconvergent transformations. Specifically, this work describes the development and mechanistic study of an enantioconvergent deborylative cyanation enabled by Cu catalysis. This method imparts a high degree of enantioselectivity and tolerates a wide range of common functional groups and heterocycles. The reaction is proposed to proceed through a radical\u2010relay mechanism. Aniline\u2010assisted homolysis of the carbon\u2013boron bond results in prochiral alkyl radicals that are functionalized by in situ generated Cu(II)(CN)\n                    <jats:sub>2<\/jats:sub>\n                    species in an enantioselective fashion. The Cu(II)(CN)\n                    <jats:sub>2<\/jats:sub>\n                    intermediate was characterized by electron paramagnetic resonance (EPR) spectroscopy, and its electronic structure was probed using density functional theory (DFT) calculations. Computational studies were carried out to corroborate the proposed radical\u2010relay mechanism.\n                  <\/jats:p>","DOI":"10.1002\/anie.202408745","type":"journal-article","created":{"date-parts":[[2024,9,12]],"date-time":"2024-09-12T12:39:01Z","timestamp":1726144741000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["Enantioconvergent Cross\u2010Nucleophile Coupling: Copper\u2010Catalyzed Deborylative Cyanation"],"prefix":"10.1002","volume":"63","author":[{"ORCID":"https:\/\/orcid.org\/0009-0001-1939-6637","authenticated-orcid":false,"given":"Jonathan","family":"Vu","sequence":"first","affiliation":[{"name":"Department of Chemistry Colorado State University  1301 Center Ave Fort Collins CO 80523\u20131872"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2758-9631","authenticated-orcid":false,"given":"Graham C.","family":"Haug","sequence":"additional","affiliation":[{"name":"Department of Chemistry Colorado State University  1301 Center Ave Fort Collins CO 80523\u20131872"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yongxian","family":"Li","sequence":"additional","affiliation":[{"name":"Department of Chemistry Colorado State University  1301 Center Ave Fort Collins CO 80523\u20131872"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0001-2211-4282","authenticated-orcid":false,"given":"Biyu","family":"Zhao","sequence":"additional","affiliation":[{"name":"Department of Chemistry Colorado State University  1301 Center Ave Fort Collins CO 80523\u20131872"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0002-1534-2719","authenticated-orcid":false,"given":"Christopher J.","family":"Chang","sequence":"additional","affiliation":[{"name":"Department of Chemistry Colorado State University  1301 Center Ave Fort Collins CO 80523\u20131872"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0104-4166","authenticated-orcid":false,"given":"Robert S.","family":"Paton","sequence":"additional","affiliation":[{"name":"Department of Chemistry Colorado State University  1301 Center Ave Fort Collins CO 80523\u20131872"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4533-4798","authenticated-orcid":false,"given":"Yuyang","family":"Dong","sequence":"additional","affiliation":[{"name":"Department of Chemistry Colorado State University  1301 Center Ave Fort Collins CO 80523\u20131872"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,10,31]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/bk-2016-1236"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2017.05.008"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-319-13054-5"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2019.04.009"},{"key":"e_1_2_7_6_1","volume-title":"Stereodirected Synthesis with Organoboranes","author":"Matteson D. 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Experimentally the oxidation of16using3was observed to proceed instantaneously consistent with a low reaction barrier."},{"key":"e_1_2_7_98_1","unstructured":"\u00a0"},{"key":"e_1_2_7_99_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b01060"},{"key":"e_1_2_7_100_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0DT02630A"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202408745","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202408745","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202408745","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,2,15]],"date-time":"2026-02-15T09:42:20Z","timestamp":1771148540000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202408745"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,10,31]]},"references-count":100,"journal-issue":{"issue":"49","published-print":{"date-parts":[[2024,12,2]]}},"alternative-id":["10.1002\/anie.202408745"],"URL":"https:\/\/doi.org\/10.1002\/anie.202408745","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,10,31]]},"assertion":[{"value":"2024-05-08","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-10-31","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202408745"}}