Intermolecular Reductive C–N Cross Coupling of Nitroarenes and Boronic Acids by P[superscript III]/P[superscript V]═O Catalysis
Name
nihms-995399.pdf
Description
Accepted version
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988.18 KB
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Author(s)
Nykaza, Trevor Vincent
Cooper, Julian Colton
Li, Gen
Mahieu, Nolwenn
Ramirez, Antonio
Luzung, Michael R.
Radosevich, Alexander T.
Date Issued
October 29, 2018
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Nykaza, Trevor V. et al. "Intermolecular Reductive C–N Cross Coupling of Nitroarenes and Boronic Acids by P[superscript III]/P[superscript V]═O Catalysis." Journal of the American Chemical Society 140, 45 (2018): 15200-15205 © 2018 American Chemical Society
Version
Author's final manuscript
Abstract
A main group-catalyzed method for the synthesis of aryl- and heteroarylamines by intermolecular C-N coupling is reported. The method employs a small-ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane) and a terminal hydrosilane reductant (phenylsilane) to drive reductive intermolecular coupling of nitro(hetero)arenes with boronic acids. Applications to the construction of both C[subscript sp2]-N (from arylboronic acids) and C[subscript sp3]–N bonds (from alkylboronic acids) are demonstrated; the reaction is stereospecific with respect to C[subscript sp3]-N bond formation. The method constitutes a new route from readily available building blocks to valuable nitrogen-containing products with complementarity in both scope and chemoselectivity to existing catalytic C-N coupling methods. Keywords: functionalization; catalysts; coupling reactions; chemical reactions; cyclization
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.
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DOI of Published Version
https://doi.org/10.1021/jacs.8b10769
