Pd-Catalyzed Tandem Isomerization/Cyclization for the Synthesis of Aromatic Oxazaheterocycles and Pyrido[3,4-b]indoles

Linglong Ding, Yan-Ning Niu and Xiao-Feng Xia*

*Key Laboratory of Synthetic and Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu 214122, China, Email: xiaxfjiangnan.edu.cn

L. Ding, Y.-N. Niu, X.-F. Xia, J. Org. Chem., 2021, 86, 10032-10042.

DOI: 10.1021/acs.joc.1c00770

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Abstract

An effient tandem process consisting of palladium-catalyzed double-bond isomerization of long-chain olefins followed by intramolecular cyclization promoted by B₂(OH)₂ provides benzo-fused oxazaheterocycles. This strategy also provides rapid access to pyrido[3,4-b]indoles, trans-2-olefins, and enamides with high regio- and stereoselectivity.

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proposed mechanism

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Key Words

benzo-fused N-Heterocycles, benzo-fused O-Heterocyles, tetrahydroxydiboron

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ID: J42-Y2021