Visible-Light/Nickel-Catalyzed Carboxylation of C(sp(2)) Bromides via Formate Activation

• Type of Material: Article
• Authors: Gavin C Smith, Emory University; Drason H Zhang, Emory University; Wanli Zhang, Emory University; Abigail H Soliven, Purdue University; William M Wuest, Emory University
• Language: English
• Date: 2023-06-15
• Publisher: AMER CHEMICAL SOC
• Publication Version: Final Published Version
• Copyright Statement: © 2023 The Authors
• License: Creative Commons Attribution 4.0 International
• Final Published Version (URL): http://dx.doi.org/10.1021/acs.joc.3c00895
• Title of Journal or Parent Work: JOURNAL OF ORGANIC CHEMISTRY
• Volume: 88
• Issue: 13
• Start Page: 9565
• End Page: 9568
• Grant/Funding Information: NIH (R35-GM119426), ACS Division of Medicinal Chemistry (G.S.),
• Keywords: NICKEL; Chemistry, Organic; Science & Technology; Chemistry; Physical Sciences; ARYL; PALLADIUM; PHOTOREDOX
• Research Categories: Chemistry, Organic

Abstract

A new visible-light-driven method for the carboxylation of (hetero)aryl/vinyl bromides has been developed using catalytic 4CzIPN, nickel, phenyl triflimide, and sodium formate as a carboxylation agent. Interestingly, we found catalytic phenyl triflimide plays an essential role in promoting the reaction. While many C(sp2) carboxylation reactions require harsh reagents or gaseous carbon dioxide, we demonstrate the mild and facile construction of carboxylic acids from readily available starting materials.