P(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C-N Coupling with Nitromethane as a Methylamine Surrogate

Gen Li, Ziyang Qin and Alexander T. Radosevich*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States, Email: radosevichmit.edu

G. Li, Z. Qin, A. T. Radosevich, J. Am. Chem. Soc., 2020, 142, 16205-16210.

DOI: 10.1021/jacs.0c08035

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Abstract

An organophosphorus-catalyzed reductive C-N coupling of nitromethane with arylboronic acid derivatives provides N-methylanilines. The small ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane P-oxide) together with phenylsilane as mild terminal reductant mediate the selective installation of the methylamino group.

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Key Words

arylamines, organocatalysis, phenylsilane

ID: J48-Y2020