Driving Recursive Dehydration by PIII/PV Catalysis: Annulation of Amines and Carboxylic Acids by Sequential C–N and C–C Bond Formation
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jacs.9b06277.pdf
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Author(s)
Lecomte, Morgan
Lipshultz, Jeffrey M.
Kim-Lee, Shin-Ho
Li, Gen
Radosevich, Alexander T.
Date Issued
July 25, 2019
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Lecomte, Morgan, Jeffrey M. Lipshultz, Shin-Ho Kim-Lee, Gen Li, and Alexander T. Radosevich, "Driving Recursive Dehydration by PIII/PV Catalysis: Annulation of Amines and Carboxylic Acids by Sequential C–N and C–C Bond Formation." Journal of the American Chemical Society 141, 32 (July 2019): p. 12507-12 doi 10.1021/jacs.9b06277 ©2019 Author(s)
Version
Final published version
Abstract
A method for the annulation of amines and carboxylic acids to form pharmaceutically relevant azaheterocycles via organophosphorus PIII/PV redox catalysis is reported. The method employs a phosphetane catalyst together with a mild bromenium oxidant and terminal hydrosilane reductant to drive successive C–N and C–C bond-forming dehydration events via the serial action of a catalytic bromophosphonium intermediate. These results demonstrate the capacity of PIII/PV redox catalysis to enable iterative redox-neutral transformations in complement to the common reductive driving force of the PIII/PV couple. ©2019
Subjects
Colloid and Surface Chemistry
Biochemistry
General Chemistry
Catalysis
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Creative Commons Attribution-NonCommercial-NoDerivs License
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DOI of Published Version
https://doi.org/10.1021/jacs.9b06277
