American Chemical Society
cs5b02524_si_001.pdf (6.56 MB)

Copper-Catalyzed Boron-Selective C(sp2)–C(sp3) Oxidative Cross-Coupling of Arylboronic Acids and Alkyltrifluoroborates Involving a Single-Electron Transmetalation Process

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journal contribution
posted on 2016-02-04, 15:27 authored by Siyi Ding, Liang Xu, Pengfei Li
A rapid and highly selective oxidative cross-coupling reaction between readily available and shelf-stable arylboronic acids and primary or secondary potassium alkyltrifluoroborates was devised and developed, which works under mild conditions using copper­(II) acetate as the catalyst and silver oxide as the oxidant. Initial experimental results indicate that a single-electron transmetalation process is involved. This approach effectively bypasses the problems associated with the traditional cross-coupling reactions of alkylboronates and thus provides a complementary method in building C­(sp2)–C­(sp3) bonds.