Oxidative lactonization of C(sp3)-H bond in methyl aromatic alcohols enabled by proton-coupled electron transfer.

Autor: Chen, Shanyi, Lai, Qihong, Liu, Chao, Liu, Hui, Huang, Mingqiang, Cai, Shunyou
Zdroj: SCIENCE CHINA Chemistry; Aug2022, Vol. 65 Issue 8, p1526-1531, 6p
Abstrakt: Direct functionalization of inert C(sp3)-H bonds in pharmaceutically significant compounds is very important in modern synthetic organic chemistry. In this article, we disclose a practical and efficient method for the oxidative lactonization of benzylic C(sp3)-H bonds enabled by the synergistic interactions of organic dye-type rose bengal, n-Bu4N·Br, O2 and Na2HPO4 under visible light irradiation. This reaction does not require transition metal catalysts or strong oxidants. A range of structurally diverse phthalides has been synthesized with excellent selectivity and high functional group compatibility. The late-stage application of this reaction to the preparation of structurally complex phthalides demonstrates its synthetic utility. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index