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Published on: May 21, 2019
Visible-Light-Driven Photocatalytic Cascade Multioxidation: A Route to α-Sulfinylphthalides
Dabao Tan1, Lele Zhang2, Qihu Yang1
1Key Laboratory of Modern Analytical Science and Separation Technology of Fujian Province, School of Chemistry Chemical Engineering, and Environment, Minnan Normal University, Zhangzhou 363000, China.
None:
The integration of direct C(sp3)-H functionalization with tandem reactions offers a strategy for the synthesis of complex, high-value fine chemicals from basic chemical feedstocks. This paper presents an efficient synthetic pathway for the olefinic difunctionalization of o-methylstyrenes using thiophenols, followed by oxidative dehydrogenative lactonization catalyzed by LaBr3 under visible light irradiation. This approach enables the facile synthesis of a wide range of α-sulfinylphthalides with moderate diastereoselectivity. Notably, the reaction does not require additional photosensitizers or strong oxidants; mild conditions suffice under an oxygen atmosphere. Mechanistic studies and control experiments have confirmed the essential role of LaBr3 in this process.
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