P(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C–N Coupling with Nitromethane as a Methylamine Surrogate
Name
nihms-1627037.pdf
Description
Accepted version
Size
1.37 MB
Format
Adobe PDF
Checksum (MD5)
711f819db12f96d0f2ecdfd903281179
Author(s)
Li, Gen
Qin, Ziyang
Radosevich, Alexander T
Date Issued
2020
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Li, Gen, Qin, Ziyang and Radosevich, Alexander T. 2020. "P(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C–N Coupling with Nitromethane as a Methylamine Surrogate." Journal of the American Chemical Society, 142 (38).
Version
Author's final manuscript
Abstract
Copyright © 2020 American Chemical Society. The direct reductive N-arylation of nitromethane by organophosphorus-catalyzed reductive C-N coupling with arylboronic acid derivatives is reported. This method operates by the action of a small ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane P-oxide) together with a mild terminal reductant hydrosilane to drive the selective installation of the methylamino group to (hetero)aromatic boronic acids and esters. This method also provides for a unified synthetic approach to isotopically labeled N-methylanilines from various stable isotopologues of nitromethane (i.e., CD3NO2, CH315NO2, and 13CH3NO2), revealing this easy-to-handle compound as a versatile precursor for the direct installation of the methylamino group.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Creative Commons Attribution-Noncommercial-Share Alike
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DOI of Published Version
https://doi.org/10.1021/JACS.0C08035
