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Heterocycle Formation via Palladium-Catalyzed Intramolecular Oxidative C-H Bond Functionalization: An Efficient Strategy for the Synthesis of 2-Aminobenzothiazoles

Laurie L. Joyce and Robert A. Batey*

*Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada, Email: rbateychem.utoronto.ca

L. L. Joyce, R. A. Batey, Org. Lett., 2009, 11, 2792-2795.

DOI: 10.1021/ol900958z (free Supporting Information)


Abstract

N-Arylthioureas are converted to 2-aminobenzothiazoles via intramolecular C-S bond formation/C-H functionalization in the presence of an unusual cocatalytic Pd(PPh3)4/MnO2 system under an oxygen atmosphere at 80C. This method eliminates the need for an ortho-halo substituted precursor, instead achieving direct functionalization of the ortho-aryl C-H bond.

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Key Words

Benzothiazoles, Oxygen


ID: J54-Y2009-1920