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

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 successi...

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Published inJournal of the American Chemical Society Vol. 141; no. 32; pp. 12507 - 12512
Main Authors Lecomte, Morgan, Lipshultz, Jeffrey M, Kim-Lee, Shin-Ho, Li, Gen, Radosevich, Alexander T
Format Journal Article
LanguageEnglish
Published American Chemical Society 14.08.2019
Subjects
Communication
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Summary: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.
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.9b06277