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  4. Cascade Palladium Catalysis: A Predictable and Selectable Regiocontrolled Synthesis of N-Arylbenzimidazoles

Cascade Palladium Catalysis: A Predictable and Selectable Regiocontrolled Synthesis of N-Arylbenzimidazoles

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Author(s)
Jui, Nathan T.
•
Buchwald, Stephen Leffler
Date Issued
October 2013
Journal
Angewandte Chemie International Edition
Publisher
John Wiley & Sons, Inc
Citation
Jui, Nathan T., and Stephen L. Buchwald. “Cascade Palladium Catalysis: A Predictable and Selectable Regiocontrolled Synthesis of N-Arylbenzimidazole.” Angewandte Chemie International Edition 52, no. 44 (October 25, 2013): 11624-11627.
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Author's final manuscript
Abstract
By choice: The palladium-catalyzed cascade reaction of 2-chloroaryl sulfonates with arylamine and amide nucleophiles provides direct access to N-arylbenzimidazoles. This strategy selectively produces the heterocycles based on chemoselective oxidative addition. 2-Chloroaryl triflates (Tf) produce one regioisomer and the corresponding 2-chloroaryl mesylates (Ms) deliver the other in a selectable manner.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
Persistent DSpace Link
http://hdl.handle.net/1721.1/85069
DOI of Published Version
https://doi.org/10.1002/anie.201306007
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