Intermolecular Reductive C-N Cross Coupling of Nitroarenes and Boronic Acids by PIII/PV=O Catalysis
Trevor V. Nykaza, Julian C. Cooper, Gen Li, Nolwenn Mahieu, Antonio Ramirez, Michael R. Luzung*, Alexander T. Radosevich*
*Bristol-Myers Squibb Company, One Squibb Drive, New Brunswick, New Jersey 08903; Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States, Email: mikekallyope.com, radosevichmit.edu
T. V. Nykaza, J. C. Cooper, G. Li, N. Mahieu, A. Ramirez, M. R. Luzung, A. T. Radosevich, J. Am. Chem. Soc., 2018, 140, 15200-15205.
DOI: 10.1021/jacs.8b10769 (free Supporting Information)
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A transition-metal-free synthesis of aryl- and heteroarylamines employs a small-ring organophosphorus-based catalyst and a terminal hydrosilane reductant to drive reductive intermolecular coupling of nitroarenes with boronic acids. Applications to the construction of both Csp2-N (from arylboronic acids) and Csp3-N bonds (from alkylboronic acids) are demonstrated; the reaction is stereospecific with respect to Csp3-N bond formation.
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