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

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

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

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Bibliographic Details
Published in:Organic letters Vol. 11; no. 13; pp. 2792 - 2795
Main Authors: Joyce, Laurie L, Batey, Robert A
Format: Journal Article
Language:English
Published: United States American Chemical Society 02-07-2009
Online Access:Get full text
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Summary:N-Arylthioureas are converted to 2-aminobenzothiazoles via intramolecular C−S bond formation/C−H functionalization utilizing an unusual cocatalytic Pd(PPh3)4/MnO2 system under an oxygen atmosphere at 80 °C. This method eliminates the need for an ortho-halo substituted precursor, instead achieving direct functionalization of the ortho-aryl C−H bond. Mechanistic observations, including a large intramolecular primary kinetic isotope effect of 5.9, reveal a reaction pathway inconsistent with an electrophilic palladation mechanism.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol900958z