Open Access
Teaching an old carbocation new tricks: Intermolecular C–H insertion reactions of vinyl cations
Stasik Popov
1
,
Brian Shao
1
,
A Bagdasarian
1
,
Tyler R Benton
1
,
Luyi Zou
1, 2
,
Zhongyue Yang
1
,
K. N. Houk
1
,
Hosea M Nelson
1
Publication type: Journal Article
Publication date: 2018-07-27
scimago Q1
wos Q1
SJR: 10.416
CiteScore: 48.4
Impact factor: 45.8
ISSN: 00368075, 10959203
PubMed ID:
30049877
Multidisciplinary
Abstract
Silicon smooths the way to vinyl cations
Saturated carbon centers often undergo substitution reactions by initial cleavage of a carbon-halogen or carbon-oxygen bond, which leaves the carbon positively charged. Analogous cations have proven much harder to access from vinylic carbons that are engaged in double bonds. Popov et al. now show that silicon cations paired with noncoordinating anions can pull triflate groups off such vinylic carbons under ambient conditions (see the Perspective by Kennedy and Klumpp). The resultant vinyl cations react with simple alkanes through C–H insertion. Theoretical and mechanistic studies suggest that these reactions proceed through nonclassical pathways that bifurcate after the transition state.
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Metrics
117
Total citations:
117
Citations from 2025:
13
(11.11%)
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GOST
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Popov S. et al. Teaching an old carbocation new tricks: Intermolecular C–H insertion reactions of vinyl cations // Science. 2018. Vol. 361. No. 6400. pp. 381-387.
GOST all authors (up to 50)
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Popov S., Shao B., Bagdasarian A., Benton T. R., Zou L., Yang Z., Houk K. N., Nelson H. M. Teaching an old carbocation new tricks: Intermolecular C–H insertion reactions of vinyl cations // Science. 2018. Vol. 361. No. 6400. pp. 381-387.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1126/science.aat5440
UR - https://doi.org/10.1126/science.aat5440
TI - Teaching an old carbocation new tricks: Intermolecular C–H insertion reactions of vinyl cations
T2 - Science
AU - Popov, Stasik
AU - Shao, Brian
AU - Bagdasarian, A
AU - Benton, Tyler R
AU - Zou, Luyi
AU - Yang, Zhongyue
AU - Houk, K. N.
AU - Nelson, Hosea M
PY - 2018
DA - 2018/07/27
PB - American Association for the Advancement of Science (AAAS)
SP - 381-387
IS - 6400
VL - 361
PMID - 30049877
SN - 0036-8075
SN - 1095-9203
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2018_Popov,
author = {Stasik Popov and Brian Shao and A Bagdasarian and Tyler R Benton and Luyi Zou and Zhongyue Yang and K. N. Houk and Hosea M Nelson},
title = {Teaching an old carbocation new tricks: Intermolecular C–H insertion reactions of vinyl cations},
journal = {Science},
year = {2018},
volume = {361},
publisher = {American Association for the Advancement of Science (AAAS)},
month = {jul},
url = {https://doi.org/10.1126/science.aat5440},
number = {6400},
pages = {381--387},
doi = {10.1126/science.aat5440}
}
Cite this
MLA
Copy
Popov, Stasik, et al. “Teaching an old carbocation new tricks: Intermolecular C–H insertion reactions of vinyl cations.” Science, vol. 361, no. 6400, Jul. 2018, pp. 381-387. https://doi.org/10.1126/science.aat5440.