Abstract

Here we report a facile, efficient, and catalyst-free method to realize C-C cross-coupling of aryl chlorides and inert arenes under UV light irradiation. The aryl radical upon homolytic cleavage of C-Cl bond initiated the nucleophilic substitution reaction with inert arenes to give biaryl products. This mild reaction mode can also be applied to other synthetic reactions, such as the construction of C-N bonds and trifluoromethylated compounds.

Highlights

  • The biaryl scaffolds are privileged constituents of natural products, pharmaceuticals, agrochemicals, dyes, and polymers [1]

  • In view of the extensive applications of biaryl intermediates in pharmaceuticals, dyestuff, and perfume, the development of efficient and catalyst-free C-C coupling methods will gain more and more attention because most catalytic methods involve the use of toxic/polluting reagents and the residues must be eliminated from the final products

  • We provided an efficient and catalyst-free method to realize C-C cross-coupling of aryl chlorides and inert arenes under UV light excitation

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Summary

Introduction

The biaryl scaffolds are privileged constituents of natural products, pharmaceuticals, agrochemicals, dyes, and polymers [1]. Transition-metal-catalyzed direct arylation of aromatic C-H bonds has been extensively developed as a valuable and efficient alternative to traditional cross-couplings in the construction of biaryl compounds [2,3,4,5,6,7] These processes suffered significant problems such as high economic cost and the presence of transition-metal impurities in the final products. We provided an efficient and catalyst-free method to realize C-C cross-coupling of aryl chlorides and inert arenes under UV light excitation This homolytic radical aromatic substitution (HAS) process gave an extremely facile mode to construct biaryl compounds, and its applicability can be extended to form diverse bonds such as trifluoromethylation and C-N cross-coupling reactions

Experimental Section
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