Pd(II)-Catalyzed Synthesis of Polycyclic Heteroarenes via an Aminopalladation/C-H Activation/Dealkylation/Decarboxylative Cyclization Cascade.

Org Lett

National & 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.

Published: October 2022

Until now, cascade reactions involving five-membered ,-palladacycles rely heavily on Pd(0)-catalyzed C-H functionalization of aryl halides initiated by carbopalladation. Herein, we report a novel Pd(II)-catalyzed cascade decarboxylative cyclization of -alkynylanilines initiated by aminopalladation. In this protocol, -alkynylanilines undergo sequential aminopalladation, C-H activation, and dealkylation to form ,-palladacycles, which are then trapped by -bromobenzoic acids or 8-bromo-1-naphthoic acid to produce diverse polycyclic heteroarenes, such as dibenzo[,]carbazoles and multiple arene-fused cyclohepta[1,2-]indoles.

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http://dx.doi.org/10.1021/acs.orglett.2c02657DOI Listing

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