Phosphonation of arenes with dialkyl phosphites catalyzed by Mn(II)/Co(II)/O2 redox couple

Takashi Kagayama; Atsushi Nakano; Satoshi Sakaguchi; Yasutaka Ishii

doi:10.1021/ol052406s

Phosphonation of arenes with dialkyl phosphites catalyzed by Mn(II)/Co(II)/O2 redox couple

Org Lett. 2006 Feb 2;8(3):407-9. doi: 10.1021/ol052406s.

Authors

Takashi Kagayama¹, Atsushi Nakano, Satoshi Sakaguchi, Yasutaka Ishii

Affiliation

¹ Department of Applied Chemistry, Faculty of Engineering, Kansai University, Suita, Osaka 564-8680, Japan.

PMID: 16435846
DOI: 10.1021/ol052406s

Abstract

[reaction: see text]. Arylphosphonates were first synthesized through a catalytic phosphonation of various arenes with dialkyl phosphites under the influence of an Mn(OAc)2/Co(OAc)2/O2 redox couple. For instance, the reaction of benzene with diethyl phosphite in the presence of Mn(OAc)2 (5 mol %) and Co(OAc)2 (1 mol %) under a mixed gas of O2 (0.5 atm) and N2 (0.5 atm) at 45 degrees C led to diethyl phenylphosphonate in 81% selectivity at 62% conversion. This is the first successful phosphonation of benzene with dialkyl phosphites through a catalytic radical process.