A regiodivergent C-H arylation of triphenylene derivatives with diaryliodonium salts was developed. The regiodivergence was controlled by electronic effects of diaryliodonium salts. When the aryl(mesityl)iodonium salts bearing strong electron-donating groups at the -position of aryl groups were used, the arylation reactions occurred to amide groups. However, if the aryl(mesityl)iodonium salts bearing electron-withdrawing groups or weak electron-donating groups at the -position of aryl groups were utilized, the arylation reactions occurred to amide groups.

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http://dx.doi.org/10.1021/acs.joc.0c02900DOI Listing

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