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One‐Pot Synthesis of Dithioacetals and Diselenoacetals: An Indium‐Catalyzed Reductive Insertion into Disulfides and Diselenides with Orthoesters as a Methylene Source
Author(s) -
Sakai Norio,
Adachi Shunpei,
Ogawa Sho,
Takahashi Kenshiro,
Ogiwara Yohei
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000053
Subject(s) - chemistry , methylene , moiety , orthoester , indium , catalysis , organic chemistry , combinatorial chemistry , malononitrile , reducing agent
The reducing system (a black hammer) composed of an indium(III) catalyst and a hydrosilane could directly and reductively drive an orthoester (a conical wedge) that functions as a masked methylene moiety into the S−S bonds of diaryl or dialkyl disulfide derivatives, providing a variety of dithioacetal derivatives. It was demonstrated that this reducing system could also be effectively adapted to the diselenoacetalization of diaryl or dialkyl diselenides. More information can be found in the Full Paper by Norio Sakai et al.