A Biphilic Phosphetane Catalyzes N-N Bond-Forming Cadogan Heterocyclization via P^III/P^V=O Redox Cycling

Trevor V. Nykaza, Tyler S. Harrison, Avipsa Ghosh, Rachel A. Putnik and Alexander T. Radosevich*

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

T. V. Nykaza, T. S. Harrison, A. Ghosh, R. A. Putnik, A. T. Radosevich, J. Am. Chem. Soc., 2017, 139, 6839-6842.

DOI: 10.1021/jacs.7b03260

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Abstract

1,2,2,3,4,4-hexamethylphosphetane catalyzes a deoxygenative N-N bond-forming Cadogan heterocyclization of o-nitrobenzaldimines and o-nitroazobenzenes with good functional group compatibility in the presence of phenylsilane as terminal reductant.

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P^III/P^V=O-Catalyzed Intermolecular N-N Bond Formation: Cross-Selective Reductive Coupling of Nitroarenes and Anilines

G. Li, S. P. Miller, A. T. Radosevich, J. Am. Chem. Soc., 2021, 143, 14464-14469.

Intermolecular Reductive C-N Cross Coupling of Nitroarenes and Boronic Acids by P^III/P^V=O Catalysis

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.

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

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

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Key Words

2H-indazoles, 2H-benzotriazoles, organocatalysis, phenylsilane

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ID: J48-Y2017