Journal
ORGANIC LETTERS
Volume 11, Issue 13, Pages 2792-2795Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol900958z
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- Natural Sciences and Engineering Research Council of Canada (NSERC)
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N-Arylthioureas are converted to 2-aminobenzothiazoles via intramolecular C-S bond formation/C-H functionalization utilizing an unusual cocatalytic Pd(PPh3)(4)/dMnO(2) system under an oxygen atmosphere at 80 degrees 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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