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Updated: Jun 27, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Al(III)-Promoted Formation of All-Carbon Quaternary Centers from Aliphatic Tertiary Chlorides and Alkynyl Silanes
Paul Charki1, Daniel S Müller1
1Univerity of Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes), UMR 6226, F-35000 Rennes, France.
Abstract:
Despite the accessibility of numerous alkynes through coupling or substitution reactions, the synthesis of trialkyl-substituted alkynes is still a major challenge. Within this context, we reexplored the electrophilic alkynyl substitution between tertiary aliphatic chlorides and silylated alkynes. We were able to demonstrate that this approach is significantly more general than originally demonstrated by Capozzi and even tolerates several functional groups. Furthermore, we report diastereoselective reactions which in some instances gave excellent diastereoselectivity (dr >95:5).
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