Photoinduced copper catalyzed nitrogen-to-alkyl radical relay Sonogashira-type coupling of -alkylbenzamides with alkynes.

Chem Commun (Camb)

Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Chang-zhou University, Changzhou, 213164, China.

Published: July 2024

This report describes a copper-catalyzed, photoinduced -to-alkyl radical relay Sonogashira-type reactions at benzylic sites in -alkylbenzamides with alkynes. The process employs an -to-alkyl radical mechanism, initiated through the copper-catalyzed reductive generation of nitrogen radicals. Radical translocation is facilitated by a 1,5-hydrogen atom transfer (1,5-HAT), leading to the formation of translocated carbon radicals. These radicals are then subjected to copper-catalyzed alkynylation. The methodology exhibits broad sub-strate scope and applicability to the synthesis of complex natural products.

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Source
http://dx.doi.org/10.1039/d4cc02861aDOI Listing

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