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Silylation of Alcohols, Phenols, and Silanols with Alkynylsilanes – an Efficient Route to Silyl Ethers and Unsymmetrical Siloxanes
Author(s) -
Kuciński Krzysztof,
Stachowiak Hanna,
Hreczycho Grzegorz
Publication year - 2020
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.202000573
Subject(s) - chemistry , organosilicon , silylation , trimethylsilyl , organic chemistry , amide , catalysis , phenols , context (archaeology) , polymer chemistry , paleontology , biology
The formation of several silyl ethers (alkoxysilanes, R 3 Si‐OR') and unsymmetrical siloxanes (R 3 Si‐O‐SiR' 3 ) can be catalyzed by the commercially available potassium bis(trimethylsilyl)amide (KHMDS). The reaction proceeds via direct dealkynative coupling between various alcohols or silanols and alkynylsilanes, with a simultaneous formation of gaseous acetylene as the sole by‐product. The dehydrogenative and dealkenative coupling of alcohols or silanols are well‐investigated, whilst the utilization of alkynylsilanes as silylating agents has never been comprehensively studied in this context. Overall, the presented system allows the synthesis of various attractive organosilicon compounds under mild conditions, making this approach an atom‐efficient, environmentally benign, and sustainable alternative to existing synthetic solutions.