Issue 7, 2022

Metal-free transfer hydrochlorination of internal C–C triple bonds with a bicyclo[3.1.0]hexane-based surrogate releasing two molecules of hydrogen chloride

Abstract

The development and application of a transfer hydrochlorination reagent based on a trichlorinated bicyclo[3.1.0]hexane core that transfers two molecules of HCl per molecule of surrogate to a π-basic substrate under B(C6F5)3 catalysis is reported. Lewis acid-assisted chloride abstraction followed by thermal electrocyclic cyclopropyl-to-allyl cation ring opening releases ring strain as a previously unexploited driving force.

Graphical abstract: Metal-free transfer hydrochlorination of internal C–C triple bonds with a bicyclo[3.1.0]hexane-based surrogate releasing two molecules of hydrogen chloride

Supplementary files

Article information

Article type
Communication
Submitted
23 Nov. 2021
Accepted
17 Dec. 2021
First published
20 Dec. 2021
This article is Open Access
Creative Commons BY license

Chem. Commun., 2022,58, 973-976

Metal-free transfer hydrochlorination of internal C–C triple bonds with a bicyclo[3.1.0]hexane-based surrogate releasing two molecules of hydrogen chloride

A. J. Weidkamp and M. Oestreich, Chem. Commun., 2022, 58, 973 DOI: 10.1039/D1CC06591B

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