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Selective Electrochemical Hydrolysis of Hydrosilanes to Silanols via Anodically Generated Silyl Cations
Author(s) -
Liang Hao,
Wang LuJun,
Ji YunXing,
Wang Han,
Zhang Bo
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202010437
Subject(s) - silylation , electrochemistry , chemistry , nucleophile , surface modification , hydrolysis , nucleophilic substitution , substrate (aquarium) , selectivity , molecule , combinatorial chemistry , hydrogen atom , inorganic chemistry , organic chemistry , catalysis , group (periodic table) , electrode , geology , oceanography
The first electrochemical hydrolysis of hydrosilanes to silanols under mild and neutral reaction conditions is reported. The practical protocol employs commercially available and cheap NHPI as a hydrogen‐atom transfer (HAT) mediator and operates at room temperature with high selectivity, leading to various valuable silanols in moderate to good yields. Notably, this electrochemical method exhibits a broad substrate scope and high functional‐group compatibility, and it is applicable to late‐stage functionalization of complex molecules. Preliminary mechanistic studies suggest that the reaction appears to proceed through a nucleophilic substitution reaction of an electrogenerated silyl cation with H 2 O.