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Heterocycle Formation via Palladium-Catalyzed Intramolecular Oxidative C−H Bond Functionalization: An Efficient Strategy for the Synthesis of 2-Aminobenzothiazoles
Abstract
N-arylthioureas are converted to 2-aminobenzothiazoles via intramolecular C-S bond formation/C-H functionalization utilizing an unusual cocatalytic Pd(PPh(3))(4)/MnO(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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Cited by
Prier, C. K., Rankic, D. A., & MacMillan, D. W. C. (2013) · Chemical Reviews · doi:10.1021/cr300503r · Cited by 9,590
Cheng, Y., Yang, J., Qu, Y., & Li, P. (2012) · Organic Letters · doi:10.1021/ol2028866 · Cited by 284
Metadata
- Authors
- Joyce, L. L., & Batey, R. A.
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2009-05-28
- Volume
- 11
- Issue
- 13
- Pages
- 2792-2795
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W2133241139
- Cited by
- 189
- References
- 0
- FWCI
- 7.66
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Heterocycle Formation via Palladium-Catalyzed Intramolecular Oxidative C−H Bond Functionalization: An Efficient Strategy for the Synthesis of 2-Aminobenzothiazoles. https://app.cochat.ai/papers/10.1021/ol900958z
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- Joyce, L. L., & Batey, R. A. (2009). Heterocycle Formation via Palladium-Catalyzed Intramolecular Oxidative C−H Bond Functionalization: An Efficient Strategy for the Synthesis of 2-Aminobenzothiazoles. Organic Letters. https://doi.org/10.1021/ol900958z
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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