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Fluoride Ion-Initiated Decarboxylation of Silyl Alkynoates to Alkynylsilanes.

ABSTRACT: This communication describes the development of a metal-free catalytic decarboxylation of silyl alkynoates to alkynylsilanes. Treatment of a silyl alkynoate with a catalytic amount of tetrabutylammonium difluorotriphenylsilicate (TBAT) in N,N-dimethylformamide at 150 °C resulted in decarboxylation to give the corresponding alkynylsilane in good to excellent yield (75 → 95%). The TBAT system was applicable to the decarboxylation of sterically demanding silyl alkynoates such as tert-butyldiphenylsilyl 3-phenylpropiolate. Mechanistic studies revealed that the tetrabutylammonium alkynoate derived from TBAT and the silyl alkynoate act as a catalyst for the decarboxylation.

SUBMITTER: Kawatsu T

PROVIDER: S-EPMC8154224 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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Fluoride Ion-Initiated Decarboxylation of Silyl Alkynoates to Alkynylsilanes.

Kawatsu Takahiro T Kataoka Sho S Fukaya Norihisa N Choi Jun-Chul JC Sato Kazuhiko K Matsumoto Kazuhiro K

ACS omega 20210503 19

This communication describes the development of a metal-free catalytic decarboxylation of silyl alkynoates to alkynylsilanes. Treatment of a silyl alkynoate with a catalytic amount of tetrabutylammonium difluorotriphenylsilicate (TBAT) in N,N-dimethylformamide at 150 °C resulted in decarboxylation to give the corresponding alkynylsilane in good to excellent yield (75 → 95%). The TBAT system was applicable to the decarboxylation of sterically demanding silyl alkynoates such as te ...[more]

PMID: 34056436

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