Photoredox-Catalyzed Synthesis of Alkylaryldiazenes: Formal Deformylative C-N Bond Formation with Alkyl Radicals

Ricardo A. Angnes, Chinmay Potnis, Shengzong Liang, Carlos Roque D. Correia* and Gerald B. Hammond*

*University of Campinas, C.P. 6154, CEP 13083-970 Campinas, São Paulo, Brazil; University of Louisville, Louisville, Kentucky 40292, United States, Email: croqueunicamp.br, gb.hammondlouisville.edu

R. A. Angnes, C. Potnis, S. Liang, C. R. D. Correia, G. B. Hammond, J. Org. Chem., 2020, 85, 4153-4164.

DOI: 10.1021/acs.joc.9b03341

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Abstract

A formal, photoredox-catalyzed, deformylative C-N bond formation enables the synthesis of alkylaryldiazenes at room temperature. The procedure employs dihydropyridines for the generation of alkyl radicals, which are then trapped by diazonium salts and reduced to the corresponding diazenes without tautomerization of the diazenes to the corresponding arylhydrazones.

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Key Words

azo compounds, diazonium salts

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ID: J42-Y2020