ACS Catalysis
ACS Catalysis
3 years ago

Transition-Metal-Free In Situ Generation of Terminal Alkenes: Synthesis of Multisubstituted Acrylamidines via Tandem sp3 C–H Olefination/sp2 C–H Arylation Reactions

Transition-Metal-Free In Situ Generation of Terminal Alkenes: Synthesis of Multisubstituted Acrylamidines via Tandem sp3 C–H Olefination/sp2 C–H Arylation Reactions
Chandragiri Sujatha, Kayambu Namitharan, Rajagopal Pothikumar
An atom-efficient, one-pot sequential approach combining transition-metal-free sp3 C–H functionalization and palladium-catalyzed sp2 C–H arylation using hypervalent aryliodine reagents to access highly substituted acrylamidines has been developed. Hypervalent aryliodine reagents play a dual role as both an oxidant for the transition-metal-free terminal olefination and also provides aryl iodides for the subsequent palladium-catalyzed alkene arylation reactions. The reaction solvent dimethyl sulfoxide (DMSO) acted as a carbon source for the olefination. The present methodology enabled the synthesis of a broad range of useful 2,3-diaryl acrylamidines.

Publisher URL: http://dx.doi.org/10.1021/acscatal.7b02819

DOI: 10.1021/acscatal.7b02819

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