34914-35-7Relevant articles and documents
Highly Efficient and Chemoselective Tertiary and Secondary Benzylation of Thiols Catalyzed by Indium(III) Triflate
Kuciński, Krzysztof,Hreczycho, Grzegorz
, p. 5572 - 5581 (2017/10/13)
Several examples of nucleophilic substitution reactions of compounds that have good leaving groups have been previously reported, but the direct use of simple alcohols still remains a challenge because of the poor leaving ability of the hydroxy group. Herein, an efficient and highly chemoselective method for the S-benzylation of a wide range of aromatic and aliphatic thiols has been accomplished in the presence of catalytic amounts (0.1–0.2 mol-%) of indium(III) triflate. Our approach is atom efficient (water is the only byproduct) and suitable to obtain the corresponding unsymmetrical thioethers in excellent yields (up to 99 %). The low loading of catalyst that are needed to obtain extraordinarily high chemoselectivities and the generality of the reaction make this approach unique.
