P III /P V ═O-Catalyzed Intermolecular N–N Bond Formation: Cross-Selective Reductive Coupling of Nitroarenes and Anilines
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nihms-1736091.pdf
Description
Accepted version
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1.22 MB
Format
Adobe PDF
Checksum (MD5)
bb73c68c8975e06073c635a6a2a6a6db
Author(s)
Li, Gen
Miller, Steven P
Radosevich, Alexander T
Date Issued
2021
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Li, Gen, Miller, Steven P and Radosevich, Alexander T. 2021. "P III /P V ═O-Catalyzed Intermolecular N–N Bond Formation: Cross-Selective Reductive Coupling of Nitroarenes and Anilines." Journal of the American Chemical Society, 143 (36).
Version
Author's final manuscript
Abstract
An organophosphorus-catalyzed method for the synthesis of unsymmetrical hydrazines by cross-selective intermolecular N-N reductive coupling is reported. This method employs a small ring phosphacycle (phosphetane) catalyst together with hydrosilane as the terminal reductant to drive reductive coupling of nitroarenes and anilines with good chemoselectivity and functional group tolerance. Mechanistic investigations support an autotandem catalytic reaction cascade in which the organophosphorus catalyst drives two sequential and mechanistically distinct reduction events via PIII/PV═O cycling in order to furnish the target N-N bond.
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.1C07272
