N-Heterocyclic carbene-catalyzed deaminative cross-coupling of aldehydes with Katritzky pyridinium salts. Issue 12 (3rd March 2020)

• Record Type: Journal Article
• Authors: Kim, Inwon; Im, Honggu; Lee, Hyeonyeong; Hong, Sungwoo
• Is Part Of: Chemical science. Volume 11:Issue 12(2020)
• Page Start: 3192
• Page End: 3197
• Publication Date: 2020-03-03
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0sc00225a
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : By employing an N-heterocyclic carbene (NHC) catalyst, we developed a versatile catalytic system that enables deaminative cross-coupling reactions of aldehydes with redox-active pyridinium salts. Abstract : By employing an N-heterocyclic carbene (NHC) catalyst, we developed a versatile catalytic system that enables deaminative cross-coupling reactions of aldehydes with redox-active pyridinium salts. Katritzky pyridinium salts behave as single-electron oxidants capable of generating alkyl radicals enabled by the redox properties of the enolate form of Breslow intermediates. The resultant alkyl radical undergoes efficient recombination with the NHC-bound aldehyde-derived carbonyl carbon radical for the formation of a C–C bond. The mild and transition metal-free reaction conditions tolerate a broad range of functional groups, and its utility has been further demonstrated by the modification of a series of peptide feedstocks and application to the three-component dicarbofunctionalization of olefins.