Green Catalysis for Three-Component Reaction of Carbon Dioxide, Propargylic Alcohols and Nucleophiles

Citation: ZHOU Zhihua, XIA Shumei, HE Liangnian. Green Catalysis for Three-Component Reaction of Carbon Dioxide, Propargylic Alcohols and Nucleophiles[J]. Acta Physico-Chimica Sinica, 2018, 34(8): 838-844. doi: 10.3866/PKU.WHXB201712271 shu

绿色催化二氧化碳、炔丙醇和亲核试剂的三组分反应

1.
南开大学元素有机化学国家重点实验室，天津 300071
2.
天津化学化工协同创新中心，天津 300071

作者简介:

HE Liangnian born in August 1964. He got his PhD degree from Nankai University in 1996. Now, he is a professor of Chemistry at Nankai University. His current research interests cover green chemistry, CO₂ chemistry, and biomass conversion;

通讯作者: 何良年, heln@nankai.edu.cn

基金项目:
国家自然科学基金 21672119

国家自然科学基金 21421062

国家重点研究和开发项目(2016YFA0602900), 国家自然科学基金(21472103, 21421001, 21421062, 21672119), 天津市自然科学基金(16JCZDJC39900)资助项目

国家自然科学基金 21421001

国家重点研究和开发项目 2016YFA0602900

国家自然科学基金 21472103

天津市自然科学基金 16JCZDJC39900

摘要: 近些年来，将CO₂转化为高附加值化学品受到广泛关注。其中，CO₂、炔丙醇和亲核试剂的三组分反应可用于制备用途广泛的羰基化合物，该方法具有步骤经济性、原子经济性等优点。由于CO₂分子具有热力学稳定性和动力学惰性，多数CO₂参与的化学反应在热力学上不支持。然而，CO₂、炔丙醇和双亲核试剂三组分反应是热力学有利的CO₂转化反应，实现了邻二醇或氨基醇和CO₂到环状碳酸酯以及2-噁唑啉酮的高效转化。本综述旨在于总结并讨论近年来CO₂、炔丙醇和亲核试剂三组分反应制备多种羰基化学物的主要进展。

关键词:

English

Green Catalysis for Three-Component Reaction of Carbon Dioxide, Propargylic Alcohols and Nucleophiles

1.
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. China
2.
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, P. R. China

Author Bio: HE Liangnian born in August 1964. He got his PhD degree from Nankai University in 1996. Now, he is a professor of Chemistry at Nankai University. His current research interests cover green chemistry, CO₂ chemistry, and biomass conversion;

Corresponding author: HE Liangnian, heln@nankai.edu.cn

Received Date: 05 December 2017
Accepted Date: 25 December 2017
Revised Date: 22 December 2017
Available Online: 15 August 2018
Fund Project:

The project was supported by the National Key Research and Development Program (2016YFA0602900), National Natural Science Foundation of China (21472103, 21421001, 21421062, 21672119), Natural Science Foundation of Tianjin Municipality (16JCZDJC39900)

Abstract: Carbon dioxide (CO₂) is one of the main greenhouse gases that can be utilized as a useful C₁ source owing to its abundance, non-toxicity, and renewability. In fact, the transformation of carbon dioxide into valuable organic molecules has attracted considerable attention over the past decades. One-pot multicomponent reactions generally proceed with more than two different raw materials reacting in one pot, thus simplifying the reaction in operation and workup. In this regard, a three-component reaction of CO₂, propargylic alcohols, and nucleophiles such as amines, water, and alcohols, to prepare useful carbonyl compounds (e.g., carbamates, oxazolidinones, α-hydroxyl ketones, and organic carbonates) is particularly appealing because of the advantages of step and atom economy. From a mechanistic point of view, the three-component reaction of CO₂, a propargylic alcohol, and a nucleophile is a type of cascade reaction, involving the carboxylative cyclization of CO₂ and propargylic alcohol, and subsequent reaction of a nucleophile with the in situ formed α-alkylidene cyclic carbonate. On the other hand, reactions involving CO₂ are generally thermodynamically unfavorable because of the thermodynamic stability and kinetic inertness of CO₂. Cyclic carbonates are widely used in organic synthesis, and their preparation from vicinal diols and CO₂ represents a green synthetic method because biomass is utilized as the source of vicinal diols. However, the low yields of cyclic carbonates are obtained in most cases because of thermodynamic limitations and deactivation of the catalyst by water, which is the co-product of cyclic carbonates. The most commonly used method to improve the yields of cyclic carbonates involves the addition of dehydrating agents. However, decreased selectivity is often observed because of the side reaction of vicinal diols with the hydrolysis products of the dehydrating agent. In addition, the reaction of 2-aminoethanols and CO₂ to obtain the corresponding 2-oxazolidinones also encounters the analogous thermodynamic limitation. To solve this problem, an efficient three-component reaction of CO₂, propargylic alcohols, and nucleophiles was developed to offer thermodynamically favorable ways for converting CO₂ into cyclic carbonates and 2-oxazolidinones with vicinal diols or 2-aminoethanols as nucleophiles. In this strategy, water is not generated and the α-alkylidene cyclic carbonate formed from CO₂ and propargylic alcohol as the actual carbonyl source reacts with vicinal diol or 2-aminoethanol to give the corresponding cyclic carbonates or 2-oxazolidinones in high yields and selectivity with the simultaneous formation of hydroxyketones. This review aims to summarize and discuss the recent advances in three-component reactions of CO₂, propargylic alcohols, and nucleophiles to prepare various carbonyl compounds promoted by both metal catalysts and organocatalysts.

Key words:

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通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

绿色催化二氧化碳、炔丙醇和亲核试剂的三组分反应

作者简介:

HE Liangnian born in August 1964. He got his PhD degree from Nankai University in 1996. Now, he is a professor of Chemistry at Nankai University. His current research interests cover green chemistry, CO₂ chemistry, and biomass conversion;

通讯作者: 何良年, heln@nankai.edu.cn

English

Green Catalysis for Three-Component Reaction of Carbon Dioxide, Propargylic Alcohols and Nucleophiles

Author Bio: HE Liangnian born in August 1964. He got his PhD degree from Nankai University in 1996. Now, he is a professor of Chemistry at Nankai University. His current research interests cover green chemistry, CO₂ chemistry, and biomass conversion;

Corresponding author: HE Liangnian, heln@nankai.edu.cn

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CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

绿色催化二氧化碳、炔丙醇和亲核试剂的三组分反应

作者简介: HE Liangnian born in August 1964. He got his PhD degree from Nankai University in 1996. Now, he is a professor of Chemistry at Nankai University. His current research interests cover green chemistry, CO2 chemistry, and biomass conversion;

通讯作者: 何良年, heln@nankai.edu.cn

English

Green Catalysis for Three-Component Reaction of Carbon Dioxide, Propargylic Alcohols and Nucleophiles

Author Bio: HE Liangnian born in August 1964. He got his PhD degree from Nankai University in 1996. Now, he is a professor of Chemistry at Nankai University. His current research interests cover green chemistry, CO2 chemistry, and biomass conversion;

Corresponding author: HE Liangnian, heln@nankai.edu.cn

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

作者简介:

HE Liangnian born in August 1964. He got his PhD degree from Nankai University in 1996. Now, he is a professor of Chemistry at Nankai University. His current research interests cover green chemistry, CO₂ chemistry, and biomass conversion;

Author Bio: HE Liangnian born in August 1964. He got his PhD degree from Nankai University in 1996. Now, he is a professor of Chemistry at Nankai University. His current research interests cover green chemistry, CO₂ chemistry, and biomass conversion;

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs