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Updated: May 1, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Preparation and reactions of heteroarylmethylzinc reagents
Nadja M Barl1, Elodie Sansiaume-Dagousset, Gabriel Monzón
1Department of Chemistry, Ludwig-Maximilians-Universität , Butenandtstrasse 5-13, 81377 Munich, Germany.
Abstract:
We report a general preparation of heteroarylmethylzinc chlorides by direct zinc insertion into heteroarylmethyl chlorides, along with a facile and straightforward synthesis of these heterocyclic chloromethyl precursors. We demonstrate that heteroarylmethylzinc reagents undergo various reactions including cross-couplings, allylations, acylations, and addition reactions to aldehydes, leading to polyfunctional heterocyclic products. Furthermore, these heteroaromatic zinc compounds prove to be versatile reagents for the preparation of various N- and O-heterocycles and give access to an analogue of a CB1 modifier.
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