华东师范大学学报（自然科学版） >

2023 , Vol. 2023 >Issue 1: 12 - 20

DOI: https://doi.org/10.3969/j.issn.1000-5641.2023.01.002

原子经济性反应

双齿含氧配体修饰Co2(CO)8催化环氧丙 (乙) 烷羰化酰胺化反应制备β-羟基酰胺

  • 郭琳 ,
  • 时广辉 ,
  • 陈晓超 ,
  • 刘晔
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  • 1. 华东师范大学 化学与分子工程学院 上海市绿色化学与化工过程绿色化重点实验室, 上海　200062
    2. 崇明生态研究院, 上海　202162

收稿日期: 2022-06-21

  录用日期: 2022-09-16

  网络出版日期: 2023-01-07

基金资助

国家自然科学基金 (22172052, 21972045)

收起

Aminocarbonylation of propylene (ethylene) epoxide over Co2(CO)8 catalyst modified by bidental O-containing ligand for synthesis of β-hydroxy amides

  • Lin GUO ,
  • Guanghui SHI ,
  • Xiaochao CHEN ,
  • Ye LIU
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  • 1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai　200062, China
    2. Institute of Eco-Chongming, Shanghai　202162, China

Received date: 2022-06-21

  Accepted date: 2022-09-16

  Online published: 2023-01-07

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摘要

首次报道了以芳香胺为氨源, 通过双齿含氧配体L2修饰Co2(CO)8催化环氧化合物的羰化酰胺化反应, 一步合成β-羟基酰胺化合物的方法. 在温和的条件下 (60℃、CO 3.0 MPa、6 h), 以L2修饰的Co2(CO)8作为催化剂, 能够实现环氧丙烷和苯胺的羰化酰胺化反应, 得到收率为64%的3-羟基-N-苯基丁酰胺目标产物; 该催化剂体系具有较好的稳定性和一定的底物普适性. 其中, 双齿含氧配体L2通过双氧水氧化双齿膦配体Xantphos (9,9-二甲基-4,5-双二苯基膦-氧杂蒽) 制得.

关键词： 环氧丙烷; 环氧乙烷; 羰化酰胺化反应; Co2(CO)8; β-羟基酰胺

本文引用格式

郭琳 , 时广辉 , 陈晓超 , 刘晔 . 双齿含氧配体修饰Co2(CO)8催化环氧丙 (乙) 烷羰化酰胺化反应制备β-羟基酰胺[J]. 华东师范大学学报（自然科学版）, 2023 , 2023(1) : 12 -20 . DOI: 10.3969/j.issn.1000-5641.2023.01.002

Abstract

This work reports a one-step protocol for the synthesis of β-hydroxyamides via amino-carbonylation of epoxides using aromatic amines as the ammonia source instead of silylamine. The reaction was catalyzed by Co2(CO)8 modified with bidentate O-containing ligand L2, which was prepared by the oxidation of Xantphos [9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene] by H2O2 as a diphosphine-dioxide. Under mild conditions (60 °C, CO 3.0 MPa, 6 h), L2-modified Co2(CO)8 efficiently catalyzed the amino-carbonylation of propylene oxide with aniline to generate 3-hydroxy-N-phenylbutanamide with the yield of 64%. The developed catalytic system exhibited fair stability and general substrate scope.

Key words： propylene oxide; ethylene oxide; aminocarbonylation; Co2(CO)8; β-hydroxy amides

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