Carboxylation of Aromatic and Aliphatic Bromides and Triflates with CO2 by Dual Visible‐Light–Nickel Catalysis. Issue 43 (18th September 2017)

• Record Type: Journal Article
• Authors: Meng, Qing‐Yuan; Wang, Shun; König, Burkhard
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 43(2017)
• Page Start: 13426
• Page End: 13430
• Publication Date: 2017-09-18
• Subjects: carbon dioxide -- carboxylation -- nickel catalysis -- photocatalysis -- visible light; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201706724
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: We report the efficient carboxylation of bromides and triflates with K2 CO3 as the source of CO2 in the presence of an organic photocatalyst in combination with a nickel complex under visible light irradiation at room temperature. The reaction is compatible with a variety of functional groups and has been successfully applied to the synthesis and derivatization of biologically active molecules. In particular, the carboxylation of unactivated cyclic alkyl bromides proceeded well with our protocol, thus extending the scope of this transformation. Spectroscopic and spectroelectrochemical investigations indicated the generation of a Ni 0 species as a catalytic reactive intermediate. Abstract : Not only good for plants, CO2 (formed in situ from K2 CO3 ) and light enabled the efficient and mild carboxylation of bromides and triflates in the presence of an organic fluorophore and a nickel complex (see scheme). A variety of functional groups were tolerated, and non‐activated cyclic alkyl bromides reacted well. The synthesis and derivatization of biologically active molecules demonstrated the applicability of the method in multistep synthesis.