期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 142, 期 3, 页码 1603-1613出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b12519
关键词
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资金
- Welch Foundation [AX-1788]
- NSF [CHE-1625963, CHE-1920057, CHE-1455061]
- NIGMS [GM134371]
Boronic acids are centrally important functional motifs and synthetic precursors. Visible light-induced borylation may provide access to structurally diverse boronates, but a broadly efficient photocatalytic borylation method that can effect borylation of a wide range of substrates, including strong C-O bonds, remains elusive. Herein, we report a general, metal-free visible light-induced photocatalytic borylation platform that enables borylation of electron-rich derivatives of phenols and anilines, chloroarenes, as well as other haloarenes. The reaction exhibits excellent functional group tolerance, as demonstrated by the borylation of a range of structurally complex substrates. Remarkably, the reaction is catalyzed by phenothiazine, a simple organic photocatalyst with MW < 200 that mediates the previously unachievable visible light-induced single electron reduction of phenol derivatives with reduction potentials as negative as approximately - 3 V versus SCE by a proton-coupled electron transfer mechanism. Mechanistic studies point to the crucial role of the photocatalyst-base interaction.
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