volume 88 issue 6 pages 4024-4027

Intramolecular 7-endo-dig-Selective Carbosilylation of Internal Alkynes Involving Silylium-Ion Regeneration

Publication typeJournal Article
Publication date2023-03-07
scimago Q2
wos Q1
SJR0.737
CiteScore6.1
Impact factor3.6
ISSN00223263, 15206904
Organic Chemistry
Abstract
A catalytic silylium-ion-promoted intramolecular alkyne carbosilylation reaction is reported. The ring closure is initiated by electrophilic activation of the C–C triple bond by a silylium ion, and the catalytic cycle is then maintained by the protodesilylation of a stoichiometrically added allylsilane reagent. Exclusive 7-endo-dig selectivity is seen, leading to a series of silylated benzocycloheptene derivatives with a fully substituted vinylsilane. Control experiments showed that the catalytically active silylium ion can also be regenerated by protodesilylation of the vinylsilane product.
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Zuo H., Klare H. F. T., Oestreich M. Intramolecular 7-endo-dig-Selective Carbosilylation of Internal Alkynes Involving Silylium-Ion Regeneration // Journal of Organic Chemistry. 2023. Vol. 88. No. 6. pp. 4024-4027.
GOST all authors (up to 50) Copy
Zuo H., Klare H. F. T., Oestreich M. Intramolecular 7-endo-dig-Selective Carbosilylation of Internal Alkynes Involving Silylium-Ion Regeneration // Journal of Organic Chemistry. 2023. Vol. 88. No. 6. pp. 4024-4027.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1021/acs.joc.3c00261
UR - https://pubs.acs.org/doi/10.1021/acs.joc.3c00261
TI - Intramolecular 7-endo-dig-Selective Carbosilylation of Internal Alkynes Involving Silylium-Ion Regeneration
T2 - Journal of Organic Chemistry
AU - Zuo, Honghua
AU - Klare, Hendrik F T
AU - Oestreich, Martin
PY - 2023
DA - 2023/03/07
PB - American Chemical Society (ACS)
SP - 4024-4027
IS - 6
VL - 88
PMID - 36881803
SN - 0022-3263
SN - 1520-6904
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2023_Zuo,
author = {Honghua Zuo and Hendrik F T Klare and Martin Oestreich},
title = {Intramolecular 7-endo-dig-Selective Carbosilylation of Internal Alkynes Involving Silylium-Ion Regeneration},
journal = {Journal of Organic Chemistry},
year = {2023},
volume = {88},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.3c00261},
number = {6},
pages = {4024--4027},
doi = {10.1021/acs.joc.3c00261}
}
MLA
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MLA Copy
Zuo, Honghua, et al. “Intramolecular 7-endo-dig-Selective Carbosilylation of Internal Alkynes Involving Silylium-Ion Regeneration.” Journal of Organic Chemistry, vol. 88, no. 6, Mar. 2023, pp. 4024-4027. https://pubs.acs.org/doi/10.1021/acs.joc.3c00261.