硒（碲）代亚膦氧化物与氨基醇和氨基酚的氧化交叉偶联：反应选择性的研究。

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

机构信息

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., 664033 Irkutsk, Russian Federation.

出版信息

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

DOI:10.1039/d1ob00287b

PMID:33861297

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%.

摘要

仲膦卤化物在温和条件下（室温，初始试剂的摩尔比为 1:1）与伯氨基醇在 CCl4/ Et3N 氧化体系中反应，选择性地将具有游离 OH 基团的卤代膦酸酰胺化学合成。在类似条件下，只有在酚羟基参与的情况下，仲膦卤化物与 1,2-或 1,3-氨基酚之间才会发生单交叉偶联，生成氨基苯卤代膦酸 O-酯。所合成的功能酰胺或酯的产率为 60-85%。