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...

Descripción completa

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
_version_ 1783698964450639872
author Kawatsu, Takahiro
Kataoka, Sho
Fukaya, Norihisa
Choi, Jun-Chul
Sato, Kazuhiko
Matsumoto, Kazuhiro
author_facet Kawatsu, Takahiro
Kataoka, Sho
Fukaya, Norihisa
Choi, Jun-Chul
Sato, Kazuhiko
Matsumoto, Kazuhiro
author_sort Kawatsu, Takahiro
collection PubMed
description [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.
format Online
Article
Text
id pubmed-8154224
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-81542242021-05-27 Fluoride Ion-Initiated Decarboxylation of Silyl Alkynoates to Alkynylsilanes Kawatsu, Takahiro Kataoka, Sho Fukaya, Norihisa Choi, Jun-Chul Sato, Kazuhiko Matsumoto, Kazuhiro ACS Omega [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. American Chemical Society 2021-05-03 /pmc/articles/PMC8154224/ /pubmed/34056436 http://dx.doi.org/10.1021/acsomega.1c01256 Text en © 2021 The Authors. Published by American Chemical Society Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Kawatsu, Takahiro
Kataoka, Sho
Fukaya, Norihisa
Choi, Jun-Chul
Sato, Kazuhiko
Matsumoto, Kazuhiro
Fluoride Ion-Initiated Decarboxylation of Silyl Alkynoates to Alkynylsilanes
title Fluoride Ion-Initiated Decarboxylation of Silyl Alkynoates to Alkynylsilanes
title_full Fluoride Ion-Initiated Decarboxylation of Silyl Alkynoates to Alkynylsilanes
title_fullStr Fluoride Ion-Initiated Decarboxylation of Silyl Alkynoates to Alkynylsilanes
title_full_unstemmed Fluoride Ion-Initiated Decarboxylation of Silyl Alkynoates to Alkynylsilanes
title_short Fluoride Ion-Initiated Decarboxylation of Silyl Alkynoates to Alkynylsilanes
title_sort fluoride ion-initiated decarboxylation of silyl alkynoates to alkynylsilanes
url 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
work_keys_str_mv AT kawatsutakahiro fluorideioninitiateddecarboxylationofsilylalkynoatestoalkynylsilanes
AT kataokasho fluorideioninitiateddecarboxylationofsilylalkynoatestoalkynylsilanes
AT fukayanorihisa fluorideioninitiateddecarboxylationofsilylalkynoatestoalkynylsilanes
AT choijunchul fluorideioninitiateddecarboxylationofsilylalkynoatestoalkynylsilanes
AT satokazuhiko fluorideioninitiateddecarboxylationofsilylalkynoatestoalkynylsilanes
AT matsumotokazuhiro fluorideioninitiateddecarboxylationofsilylalkynoatestoalkynylsilanes

Ejemplares similares