Intermolecular 1,2-Difunctionalization of Terminal Alkynes to Access Trisubstituted Alkenes via Copper/Photoredox Dual Catalysis

作者:Tang, Fei; Feng, Yi-Si*; Cheng, Zhi-Fei; Zhang, Qi*; Xu, Hua-Jian*
来源:Organic Letters, 2023, 25(21): 3916-3921.
DOI:10.1021/acs.orglett.3c01267

摘要

Wereport a copper metallaphotocatalytic 1,2-difunctionalizationof terminal alkynes with N-hydroxyphthalimide (NHP)esters and readily available silyl reagents (TMSCN and TMSNCS) toaccess stereodefined trisubstituted alkenes, including (E)-alkenyl nitriles and thiocyanates. The reaction proceeds with excellent anti-stereoselectivity and demonstrates broad compatibilitywith a wide range of terminal alkynes and NHP esters as alkyl radicalprecursors. Experimental and computational studies have been performedto gain insight into the reaction mechanism.