Divergent pathway and reactivity control of intramolecular arene C–H vinylation by vinyl cations

Xin Li; Shuo-Qing Zhang; Xin Hong

doi:10.1039/C9OB01916B

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Divergent pathway and reactivity control of intramolecular arene C–H vinylation by vinyl cations†

Xin Li,^a Shuo-Qing Zhang*^a and Xin Hong

*^a

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* Corresponding authors

^a Department of Chemistry, Zhejiang University, Hangzhou 310027, China
E-mail: angellasty@zju.edu.cn, hxchem@zju.edu.cn

Abstract

Vinyl cations exhibit remarkable reactivity towards arene C–H functionalizations. This computational study revealed the key mechanistic details of intramolecular C–H vinylation through a vinyl cation intermediate. Based on the reaction mechanism, the effects of substitution, ring strain and tether length on the reactivity of the vinyl cation were elucidated.

This article is part of the themed collection: Mechanistic, computational & physical organic chemistry in OBC

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DOI: https://doi.org/10.1039/C9OB01916B
Article type: Communication
Submitted: 01 sep. 2019
Accepted: 02 oct. 2019
First published: 03 oct. 2019

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Org. Biomol. Chem., 2019,17, 9135-9139

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Divergent pathway and reactivity control of intramolecular arene C–H vinylation by vinyl cations

X. Li, S. Zhang and X. Hong, Org. Biomol. Chem., 2019, 17, 9135 DOI: 10.1039/C9OB01916B

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Organic & Biomolecular Chemistry

Divergent pathway and reactivity control of intramolecular arene C–H vinylation by vinyl cations†

Abstract

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Divergent pathway and reactivity control of intramolecular arene C–H vinylation by vinyl cations

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