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Indium‐Catalyzed Reductive Sulfidation of Esters by Using Thiols: An Approach to the Diverse Synthesis of Sulfides
Author(s) -
Miyazaki Takahiro,
Kasai Shinsei,
Ogiwara Yohei,
Sakai Norio
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501559
Subject(s) - chemistry , catalysis , trifluoromethyl , benzoic acid , indium , organic chemistry , hammett equation , reductive elimination , ring (chemistry) , medicinal chemistry , combinatorial chemistry , reaction rate constant , kinetics , alkyl , physics , quantum mechanics
A new reductive preparation of unsymmetrical sulfides from esters and thiols in the presence of InI 3 and either 1,1,3,3‐tetramethyldisiloxane (TMDS) or PhSiH 3 as the reductant was developed. This protocol was applied to not only benzoic acid esters that have a methoxy, methyl, chloro, bromo, iodo, or trifluoromethyl group on the aromatic ring but also aliphatic acid esters with either aromatic or aliphatic thiols. A reaction mechanism is proposed by using Hammett plot results and several control experiments.