Tosylhydrazide-Induced 1,6-Enyne Radical Cyclization under Copper Catalysis: Access to 3,4-Dihydronaphthalen-1(2H)-one Derivatives

2024/08/30 by Yeganeh Sadat Hosseini Nasab, Saideh Rajai-Daryasarei, Saideh Rajai‐Daryasarei +3
Chemistry · #Sulfur-Based Synthesis Techniques #Radical Photochemical Reactions #Catalytic C–H Functionalization Methods

paper · doi:10.1021/acs.joc.4c01746

Abstract

We describe an approach to access 4-aroyl-3-aryl-3,4-dihydronaphthalen-1(2 H )-one derivatives in 41–79% yields through the Cu-catalyzed radical cyclization/desulfonylation of 1,6-enynes with tosylhydrazide under air conditions. This alternative desulfonylation strategy combines mild conditions, external oxidant-free processes, and sustainability, contributing to more environmentally friendly organic synthesis. The mechanistic studies showed that the CuCl/O 2 combination serves as the source of the oxygen atom needed to form the C═O bond. The existence of tosylhydrazide is crucial for this conversion.

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