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Updated: Jan 11, 2026
Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Photocatalytic Site-Selective Addition of Carbazole C(sp2)-H Bonds to Aroylformates: Synthesis of α-Quaternary
Rongfang Liu1, Hong'en Tong2, Yiqing Li2
1College of Traditional Chinese Medicine and Food Engineering, Shanxi University of Chinese Medicine, Jinzhong 030619, P. R. China.
Abstract:
The rapid advancement of organophotochemistry has established radical-mediated nucleophilic addition as a prominent strategy for carbonyl functionalization. Nevertheless, the direct addition of aryl C(sp2)-H bonds to carbonyl groups via the radical process remains largely unexplored. Herein, we report a visible-light-driven site-selective addition of carbazole C(sp2)-H bonds to aroylformates, which leads to the synthesis of a series of α-quaternary α-hydroxyesters bearing a carbazole scaffold in generally high yields. Mechanistic investigation revealed that the reaction is initiated with reductive quenching of the excited photocatalyst by carbazole and proceeds via a radical-radical cross-coupling process.
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