{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Sakai HA"],"funding":["Princeton University","Bristol-Myers Squibb","Celgene","Genentech","Pfizer","National Institute of General Medical Sciences","Merck","NIGMS NIH HHS","Princeton Catalysis Initiative","Janssen Pharmaceuticals"],"pagination":["11691-11697"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC7750884"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["142(27)"],"pubmed_abstract":["Alkyl chlorides are bench-stable chemical feedstocks that remain among the most underutilized electrophile classes in transition metal catalysis. Overcoming intrinsic limitations of C(sp<sup>3</sup>)-Cl bond activation, we report the development of a novel organosilane reagent that can participate in chlorine atom abstraction under mild photocatalytic conditions. In particular, we describe the application of this mechanism to a dual nickel/photoredox catalytic protocol that enables the first cross-electrophile coupling of unactivated alkyl chlorides and aryl chlorides. Employing these low-toxicity, abundant, and commercially available organochloride building blocks, this methodology allows access to a broad array of highly functionalized C(sp<sup>2</sup>)-C(sp<sup>3</sup>) coupled adducts, including numerous drug analogues."],"journal":["Journal of the American Chemical Society"],"pubmed_title":["Cross-Electrophile Coupling of Unactivated Alkyl Chlorides."],"pmcid":["PMC7750884"],"funding_grant_id":["R35 GM134897","R35GM134897-01"],"pubmed_authors":["Le CC","MacMillan DWC","Sakai HA","Liu W"],"additional_accession":[]},"is_claimable":false,"name":"Cross-Electrophile Coupling of Unactivated Alkyl Chlorides.","description":"Alkyl chlorides are bench-stable chemical feedstocks that remain among the most underutilized electrophile classes in transition metal catalysis. Overcoming intrinsic limitations of C(sp<sup>3</sup>)-Cl bond activation, we report the development of a novel organosilane reagent that can participate in chlorine atom abstraction under mild photocatalytic conditions. In particular, we describe the application of this mechanism to a dual nickel/photoredox catalytic protocol that enables the first cross-electrophile coupling of unactivated alkyl chlorides and aryl chlorides. Employing these low-toxicity, abundant, and commercially available organochloride building blocks, this methodology allows access to a broad array of highly functionalized C(sp<sup>2</sup>)-C(sp<sup>3</sup>) coupled adducts, including numerous drug analogues.","dates":{"release":"2020-01-01T00:00:00Z","publication":"2020 Jul","modification":"2025-04-04T01:39:54.344Z","creation":"2021-02-20T20:47:50Z"},"accession":"S-EPMC7750884","cross_references":{"pubmed":["32564602"],"doi":["10.1021/jacs.0c04812"]}}