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Gold Catalyzed Decarboxylative Cross-Coupling of Iodoarenes.
Daley, Ryan A; Morrenzin, Aaron S; Neufeldt, Sharon R; Topczewski, Joseph J.
Affiliation
  • Daley RA; Department of Chemistry, University of Minnesota Twin Cities, Minneapolis, Minnesota 55455, United States.
  • Morrenzin AS; Department of Chemistry and Biochemistry, Montana State University, Bozeman, Montana 59717, United States.
  • Neufeldt SR; Department of Chemistry and Biochemistry, Montana State University, Bozeman, Montana 59717, United States.
  • Topczewski JJ; Department of Chemistry, University of Minnesota Twin Cities, Minneapolis, Minnesota 55455, United States.
J Am Chem Soc ; 142(30): 13210-13218, 2020 07 29.
Article in En | MEDLINE | ID: mdl-32634305
ABSTRACT
This report details a decarboxylative cross-coupling of (hetero)aryl carboxylates with iodoarenes in the presence of a gold catalyst (>25 examples, up to 96% yield). This reaction is site specific, which overcomes prior limitations associated with gold catalyzed oxidative coupling reactions. The reactivity of the (hetero)aryl carboxylate correlates qualitatively to the field effect parameter (Fortho). Reactions with isolated gold complexes and DFT calculations support a mechanism proceeding through oxidative addition at a gold(I) cation with decarboxylation being viable at either a gold(I) or a silver(I) species.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: J Am Chem Soc Year: 2020 Type: Article Affiliation country: United States
Fulltext
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PubMed Links
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: J Am Chem Soc Year: 2020 Type: Article Affiliation country: United States