Co(II)/Ag(I) Synergistically Catalyzed Monoinsertion Reaction of Isocyanide to Terminal Alkynes with HO: Synthesis of Alkynamide Derivatives.

Org Lett

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology , Soochow University, Suzhou 215123 , China.

Published: September 2018

A Co(II)/Ag(I) synergistically catalyzed three-component reaction of isocyanide with terminal alkyne and water to afford alkynamide derivatives is reported. The insertion of monoisocyanide into the C-H bond of terminal alkynes is an efficient, straightforward, atom-economical route to alkynamides, which are useful synthons in organic synthesis. This synergistic process achieves the cleavage of a C-H bond and the construction of new C-C and C═O bonds under mild conditions through the reaction of Co(II)-activated isocyanides and a Ag(I)-complex-activated terminal alkyne. This reaction has broad substrate versatility and functional group tolerance.

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http://dx.doi.org/10.1021/acs.orglett.8b02516DOI Listing

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