Oxidative cross-coupling of secondary phosphine chalcogenides with amino alcohols and aminophenols: aspects of the reaction chemoselectivity

Kseniya O Khrapova; Anton A Telezhkin; Pavel A Volkov; Lyudmila I Larina; Dmitry V Pavlov; Nina K Gusarova; Boris A Trofimov

doi:10.1039/d1ob00287b

Oxidative cross-coupling of secondary phosphine chalcogenides with amino alcohols and aminophenols: aspects of the reaction chemoselectivity

Org Biomol Chem. 2021 Jun 16;19(23):5098-5107. doi: 10.1039/d1ob00287b.

Authors

Kseniya O Khrapova¹, Anton A Telezhkin¹, Pavel A Volkov¹, Lyudmila I Larina¹, Dmitry V Pavlov¹, Nina K Gusarova¹, Boris A Trofimov¹

Affiliation

¹ A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., 664033 Irkutsk, Russian Federation. boris_trofimov@irioch.irk.ru.

PMID: 33861297
DOI: 10.1039/d1ob00287b

Abstract

Secondary phosphine chalcogenides react with primary amino alcohols under mild conditions (room temperature, molar ratio of the initial reagents 1 : 1) in a CCl4/Et3N oxidizing system to chemoselectively deliver amides of chalcogenophosphinic acids with free OH groups. Under similar conditions, mono-cross-coupling between secondary phosphine chalcogenides and 1,2- or 1,3-aminophenols proceeds only with the participation of phenolic hydroxyl to give aminophenylchalcogenophosphinic O-esters. The yields of the synthesized functional amides or esters are 60-85%.