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A Biphilic Phosphetane Catalyzes N-N Bond-Forming Cadogan Heterocyclization via PIII/PV=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 (free Supporting Information)


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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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Key Words

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


ID: J48-Y2017