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Radical Arylation of Triphenyl Phosphite Catalyzed by Salicylic Acid: Mechanistic Investigations and Synthetic Applications

Manel Estruch-Blasco, Diego Felipe-Blanco, Irene Bosque and José C. González-Gómez*

*Instituto de Sı́ntesis Orgánica (ISO) and Departamento de Quı́mica Orgánica, Facultad de Ciencias, Universidad de Alicante, Apartado 99, 03080 Alicante, Spain, Email: josecarlos.gonzalezua.es

M. Estruch-Blasco, D. Felipe-Blanco, I. Bosque, J. C. González-Gómez, J. Org. Chem., 2020, 85, 14473-14485.

DOI: 10.1021/acs.joc.0c00795 (free Supporting Information)



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Abstract

A catalytic amount of inexpensive salicylic acid promotes a straightforward and scalable synthesis of diphenyl arylphosphonates from anilines and triphenyl phosphite at 20°C within 1-2 h. The reaction proceeds via radical-radical coupling and tolerates a wide range of functional groups.

 

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proposed mechanism



Key Words

Phosphonates, Sandmeyer Reaction, Organocatalysis, tert-Butyl nitrite


ID: J42-Y2020