Hydrophosphorylation of alkenes with dialkyl phosphites catalyzed by Mn(III) under air

Osamu Tayama; Atsushi Nakano; Takahiro Iwahama; Satoshi Sakaguchi; Yasutaka Ishii

doi:10.1021/jo049657j

Hydrophosphorylation of alkenes with dialkyl phosphites catalyzed by Mn(III) under air

J Org Chem. 2004 Aug 6;69(16):5494-6. doi: 10.1021/jo049657j.

Authors

Osamu Tayama¹, Atsushi Nakano, Takahiro Iwahama, Satoshi Sakaguchi, Yasutaka Ishii

Affiliation

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

PMID: 15287806
DOI: 10.1021/jo049657j

Abstract

A facile method for the synthesis of organophosphonates from alkenes and dialkyl phosphites was developed by the use of Mn(II) under air. Thus, the reaction of 1-octene with diethyl phosphite in the presence of Mn(OAc)2 (5 mol %) under air at 90 degrees C led to diethyl octylphosphonate (78%) and diethyl (2-hexyl)decylphosphonate (6%). Internal alkenes such as cis-2-octene gave a regioisomeric mixture of the corresponding hydrophosphorylation products in 84% yields.