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†
Andreas J.
Weidkamp 
a
and
Martin
Oestreich
*a
a
and
Martin
Oestreich
*a
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](/ko/Image/Get?imageInfo.ImageType=GA&imageInfo.ImageIdentifier.ManuscriptID=D1CC06591B&imageInfo.ImageIdentifier.Year=2022)
- This article is part of the themed collection: Boron Chemistry in the 21st Century: From Synthetic Curiosities to Functional Molecules
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