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Palladium-Catalyzed Oxidant Dependent Switchable Aza-Wacker Cyclization and Oxidative Dimerization of Benzimidates

Rodney A. Fernandes* and Ashvin J. Gangani

*Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, Maharashtra, India, Email: rfernandchem.iitb.ac.in

R. A. Fernandes, A. J. Gangani, Org. Lett., 2022, 24, 7400-7404.

DOI: 10.1021/acs.orglett.2c02924



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Abstract

Whereas the reaction of O-homoallyl benzimidates with Cu(OAc)2 as oxidant involved an aza-Wacker-type intramolecular cyclization under Pd-catalysis to deliver 4-methylene-1,3-oxazines, K2S2O8 as oxidant promotes a dimerization of O-homoallyl benzimidates to yield benzohydrazonates (azines).

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proposed mechanism



Key Words

N-heterocycles, O-heterocycles, Copper(II)


ID: J54-Y2022