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Ligand‐Controlled Regiodivergent Thiocarbonylation of Alkynes toward Linear and Branched α,β‐Unsaturated Thioesters
Author(s) -
Ai HanJun,
Lu Wangyang,
Wu XiaoFeng
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202106079
Subject(s) - chemistry , regioselectivity , ligand (biochemistry) , selectivity , phosphine , ether , boronic acid , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , receptor , biochemistry
Thiocarbonylation of alkynes offers an ideal procedure for the synthesis of unsaturated thioesters. A robust ligand‐controlled regioselective thiocarbonylation of alkynes is developed. Utilizing boronic acid and 5‐chlorosalicylic acid as the acid additive to in situ form 5‐chloroborosalicylic acid (5‐Cl‐BSA), and bis(2‐diphenylphosphinophenyl)ether (DPEphos) as the ligand, linear α,β‐unsaturated thioesters were produced in a straightforward manner. Switching the ligand to tri(2‐furyl)phosphine can turn the reaction selectivity to give branched products. Remarkably, this approach also represents the first example on thiocarbonylation of internal alkynes.