Driving Recursive Dehydration by PIII/PV Catalysis: Annulation of Amines and Carboxylic Acids by Sequential C–N and C–C Bond Formation

Author(s)
Lecomte, Morgan; Lipshultz, Jeffrey M.; Kim-Lee, Shin-Ho; Li, Gen; Radosevich, Alexander T.
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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
Date issued
2019-07-25
URI
https://hdl.handle.net/1721.1/124882
Department
Massachusetts Institute of Technology. Department of Chemistry
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
ISSN
0002-7863
1520-5126
Keywords
Colloid and Surface Chemistry, Biochemistry, General Chemistry, Catalysis
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