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Fluoride Ion-Initiated Decarboxylation of Silyl Alkynoates to Alkynylsilanes

[Image: see text] 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...

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Detalles Bibliográficos
Autores principales: Kawatsu, Takahiro, Kataoka, Sho, Fukaya, Norihisa, Choi, Jun-Chul, Sato, Kazuhiko, Matsumoto, Kazuhiro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8154224/
https://www.ncbi.nlm.nih.gov/pubmed/34056436
http://dx.doi.org/10.1021/acsomega.1c01256
Descripción
Sumario:[Image: see text] 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.