Metal-free thioesterification of α,β-unsaturated aldehydes with thiols

被引:7
作者
Bolt, Malgorzata [1 ]
Hanek, Kamil [1 ]
Zak, Patrycja [1 ]
机构
[1] Adam Mickiewicz Univ, Fac OfChem, Dept Organometall Chem, Uniwersytetu Poznanskiego 8, PL-61614 Poznan, Poland
关键词
N-HETEROCYCLIC CARBENE; SULFA-MICHAEL ADDITION; ENANTIOSELECTIVE BETA-PROTONATION; CATALYZED SYNTHESIS; THIOESTERS; UMPOLUNG; ENALS;
D O I
10.1039/d2qo00678b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
For the first time, the synthesis of thioesters starting from enals and thiols has been performed in the presence of a bulky N-heterocyclic carbene (NHC) as a catalyst. This new method has been proved to be effective with a wide substrate scope giving selective thioesters in yields above 85% under mild and metal-free conditions. This green protocol does not require elevated temperatures, or addition of oxidants or other additives. The steric bulk of the carbene was found to markedly influence the reaction chemoselectivity. Bulky NHC carbene ligands, in contrast to those with less sterically developed ligands, completely change the chemoselectivity of the reaction leading to 1,2-addition products and not sulfa-Michael addition (SMA) adducts.
引用
收藏
页码:4846 / 4853
页数:8
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