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However, the utilization of unactivated alkyl halides in such a transformation remains a formidable challenge. In this study, we developed a cross\u2010coupling reaction of aldehydes with unactivated alkyl halides through N\u2010heterocyclic carbene catalysis. With this protocol, various ketones could be rapidly synthesized from readily available starting materials under mild conditions. This organocatalytic system was successfully applied in the late\u2010stage functionalization of pharmaceutical derivatives. Mechanistic investigations suggest a closed\u2010shell nucleophilic substitution mechanism for this reaction.<\/jats:p>","DOI":"10.1002\/anie.202309572","type":"journal-article","created":{"date-parts":[[2023,8,16]],"date-time":"2023-08-16T15:40:37Z","timestamp":1692200437000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":28,"title":["Direct Acylation of Unactivated Alkyl Halides with Aldehydes through N\u2010Heterocyclic Carbene Organocatalysis"],"prefix":"10.1002","volume":"62","author":[{"given":"Qing\u2010Zhu","family":"Li","sequence":"first","affiliation":[{"name":"Anti-infective Agent Creation Engineering Research Centre of Sichuan Province Sichuan Industrial Institute of Antibiotics School of Pharmacy Chengdu University  Chengdu 610106 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rong","family":"Zeng","sequence":"additional","affiliation":[{"name":"Anti-infective Agent Creation Engineering Research Centre of Sichuan Province Sichuan Industrial Institute of Antibiotics School of Pharmacy Chengdu University  Chengdu 610106 China"},{"name":"State Key Laboratory of Southwestern Chinese Medicine Resources School of Pharmacy Chengdu University of Traditional Chinese Medicine  Chengdu 611137 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peng\u2010Shuai","family":"Xu","sequence":"additional","affiliation":[{"name":"Anti-infective Agent Creation Engineering Research Centre of Sichuan Province Sichuan Industrial Institute of Antibiotics School of Pharmacy Chengdu University  Chengdu 610106 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xin\u2010Hang","family":"Jin","sequence":"additional","affiliation":[{"name":"Anti-infective Agent Creation Engineering Research Centre of Sichuan Province Sichuan Industrial Institute of Antibiotics School of Pharmacy Chengdu University  Chengdu 610106 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chuan","family":"Xie","sequence":"additional","affiliation":[{"name":"Anti-infective Agent Creation Engineering Research Centre of Sichuan Province Sichuan Industrial Institute of Antibiotics School of Pharmacy Chengdu University  Chengdu 610106 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qi\u2010Chun","family":"Yang","sequence":"additional","affiliation":[{"name":"Anti-infective Agent Creation Engineering Research Centre of Sichuan Province Sichuan Industrial Institute of Antibiotics School of Pharmacy Chengdu University  Chengdu 610106 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiang","family":"Zhang","sequence":"additional","affiliation":[{"name":"Anti-infective Agent Creation Engineering Research Centre of Sichuan Province Sichuan Industrial Institute of Antibiotics School of Pharmacy Chengdu University  Chengdu 610106 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4700-0142","authenticated-orcid":false,"given":"Jun\u2010Long","family":"Li","sequence":"additional","affiliation":[{"name":"Anti-infective Agent Creation Engineering Research Centre of Sichuan Province Sichuan Industrial Institute of Antibiotics School of Pharmacy Chengdu University  Chengdu 610106 China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,8,25]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"\u00a0"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.1039\/b100919m"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar300054e"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/pi.5624"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.8b01022"},{"key":"e_1_2_3_6_1","unstructured":"\u00a0"},{"key":"e_1_2_3_7_2","volume-title":"The Logic of Chemical Synthesis","author":"Corey E. 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