Litcius/Paper detail

Photochemical (Hetero-)Arylation of Aryl Sulfonium Salts

Yue Zhao, Congjun Yu, Wenjing Liang, Frédéric W. Patureau

2021Organic Letters89 citationsDOIOpen Access PDF

Abstract

The construction of (hetero)biaryls, which are ubiquitous scaffolds among medical substances, functional materials, and agrochemicals, constitutes a key application of cross-coupling methods. However, these usually require multiple synthetic steps. Herein, we report a simple photoinduced and catalyst-free C-H/C-H (hetero)arylation cross-coupling through aryl thianthrenium salts, which are formed site-selectively by direct C-H functionalization. The key to this approach is the UV-light, which can disrupt the C-S bond to form thianthrene radical cations and aryl radicals.

Topics & Concepts

SulfoniumChemistryArylThianthreneCombinatorial chemistryRadicalPhotochemistryCatalysisSurface modificationMoleculeSalt (chemistry)Organic chemistryAlkylPhysical chemistrySulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods