Anthranilamide-protected Vinylboronic Acid: Rational Monomer Design for Improved Polymerization/transformation Ability Providing Access to Conventionally Inaccessible Copolymers

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 Dec 15

PMID 36519042

Authors

Hiroshi Suzuki

Tsuyoshi Nishikawa

Hiroshi Makino

Makoto Ouchi

Affiliations

Soon will be listed here.

Abstract

We have studied several protecting groups for vinylboronic-acid derivatives as monomers in radical polymerizations with the objective to improve the polymerization ability and C-B bond-cleaving post-transformation performance. Anthranilamide (aam)-protected vinylboronic acid (VBaam) exhibited experimentally a relatively high polymerization activity, which was theoretically corroborated by density functional theory (DFT) calculations that revealed a peculiar effect of the interaction between the aam groups on the polymerization behavior. The VBaam units in the copolymers can subsequently be transformed into vinyl alcohols or into ethylene units through C-B-bond-cleaving side-chain replacement, which affords valuable copolymers such as poly(vinyl alcohol--styrene), poly(ethylene--styrene), and poly(ethylene--acrylate).

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