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

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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Publication details

The article was received on 01 Sep 2019, accepted on 02 Oct 2019 and first published on 03 Oct 2019

Article type: Communication

DOI: 10.1039/C9OB01916B

Citation: Org. Biomol. Chem., 2019, Advance Article

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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, Advance Article , 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

Supplementary files

Publication details

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

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