Premium
Silylating Disulfides and Thiols with Hydrosilicones Catalyzed by B(C 6 F 5 ) 3
Author(s) -
Liao Mengchen,
Zheng Sijia,
Brook Michael A.
Publication year - 2021
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.202100349
Subject(s) - chemistry , thio , silylation , siloxane , catalysis , silane , reactivity (psychology) , steric effects , cleave , sulfur , thiol , medicinal chemistry , silicone , polymer chemistry , organic chemistry , enzyme , medicine , alternative medicine , pathology , polymer
Hydrosilanes and silicones, catalyzed with B(C 6 F 5 ) 3 , may be used to silylate thiols or cleave disulfides giving silyl thio ethers. Alcohols were found to react faster than thiols or disulfides, while alkoxysilanes (the Piers‐Rubinsztajn reaction) were slower such that the overall order of reactivity was found to be HO>HS>SS>SiOEt. The resulting silane and silicone‐protected thio ethers produced from the sulfur‐based functional groups could be cleaved to thiols using alcohols or mild acid with rates that depend on the steric bulk of the siloxane.