Palladium-Catalyzed Synthesis of Triphenylenes via Sequential C-H Activation and Decarboxylation
Yuzhong Yang1, Bang Zhou1, Xiaoming Zhu1
1National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province , Hunan Normal University , Changsha , Hunan 410081 , China.
Abstract:
A novel tandem intermolecular decarboxylative coupling reaction of o-bromobenzoic acids and aryl iodides has been developed. The method affords a range of unsymmetrically triphenylenes and displays unique regioselectivity and broad substrate scope. Mechanistically, palladium/norbornene-catalyzed C-H activation and subsequent double decarboxylative coupling reactions were involved. Moreover, the triphenylenes can also be synthesized from 2-iodobiphenyls and o-bromobenzoic acids under norbornene-free conditions.
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