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Updated: Aug 2, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Synthesizing Complex Quaternary Carbons by the Sequence-Regulated Additions of tert-Alkyl Radicals to Two Different
Kyosuke Matsuda1, Chihiro Tanaka1, Daisuke Sato1
1Graduate School of Science and Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube, Yamaguchi 755-8611, Japan.
Abstract:
We report the sequence-regulated radical additions of tert-alkyl radicals to two different olefins controlled by a Cu catalyst, which we term the "atom-transfer radical addition-substitution" reaction. The reactions of α-bromocarbonyl compounds, such as tert-alkyl radical sources, with methacrylates and styrenes occur in a sequence-regulated manner to give the corresponding three-component product possessing skipped quaternary carbon centers. Our method provides new insight into how to control the reactivities of tert-alkyl radicals during the synthesis of regulated aliphatic chains.
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