Driving Recursive Dehydration by PIII/PV Catalysis: Annulation of Amines and Carboxylic Acids by Sequential C–N and C–C Bond Formation
| Autor: | Gen Li, Morgan Lecomte, Jeffrey M. Lipshultz, Alexander T. Radosevich, Shin‐Ho Kim‐Lee |
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| Přispěvatelé: | Massachusetts Institute of Technology. Department of Chemistry |
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
Annulation
Nitrogen Carboxylic Acids 010402 general chemistry 01 natural sciences Redox Biochemistry Catalysis Colloid and Surface Chemistry Heterocyclic Compounds medicine Dehydration Amines Chemistry Extramural Carbon chemistry Communication Oxidation reduction General Chemistry Bond formation medicine.disease Combinatorial chemistry Carbon 3. Good health 0104 chemical sciences Cyclization Oxidation-Reduction |
| Zdroj: | Journal of the American Chemical Society ACS |
| ISSN: | 1520-5126 0002-7863 |
| Popis: | 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 NIH NIGMS (grant no. GM114547) |
| Databáze: | OpenAIRE |
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