铜氢催化不饱和烃与醛、酮的亲核加成反应

引用本文: 赵悦, 李雁飞, 熊涛. 铜氢催化不饱和烃与醛、酮的亲核加成反应[J]. 大学化学, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001 shu

Citation: Yue Zhao, Yanfei Li, Tao Xiong. Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones[J]. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001 shu

铜氢催化不饱和烃与醛、酮的亲核加成反应

东北师范大学化学学院, 长春 130024

通讯作者: 熊涛, xiongt626@nenu.edu.cn

基金项目:
国家自然科学基金(22193012,22171042)

吉林省自然科学基金(20210101134JC)

摘要: 金属有机试剂(如：有机锂试剂、格氏试剂、有机铜试剂及有机铝试剂)对醛、酮的加成反应是有机化学中的重要反应，也是最经典的构建C―C键的方法之一。然而上述金属有机试剂存在官能团兼容性较差、对水和空气敏感及不易存储等缺陷，不可避免地限制了其广泛应用。近年来，利用稳定、易得的不饱和烃为原料替代金属有机试剂参与各种化学转化受到了人们高度关注。本文主要介绍在铜氢催化条件下，通过把不饱和烃现场转化为催化量有机铜中间体替代传统化学计量金属有机试剂的策略，实现其对醛、酮的加成反应，从而避免了传统方法的缺点。对于上述反应的介绍，能够丰富和拓展基础教学过程中亲核加成知识点的内容，开阔学生的视野与思维，有利于学生了解学科前沿领域的发展现状，激发学生的兴趣。

关键词:

English

Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones

Department of Chemistry, Northeast Normal University, Changchun 130024, China

Corresponding author: Tao Xiong, xiongt626@nenu.edu.cn

Received Date: 01 September 2023
Revised Date: 16 January 2024
Available Online: 06 February 2024

Abstract: The addition reactions of organometallics such as organolithium reagents, Grignard reagent, organocopper reagents and organoaluminum reagents to aldehydes and ketones are crucial in organic chemistry, and represent one of most classic methods for C―C bond construction. However, such organometallics are limited in their wide applications due to their poor functional group compatibility, sensitivity to water and air and difficulties in storage. As a consequence, the development of new methods with stable, readily available unsaturated hydrocarbons instead of organometallics to participate in various transformations have attracted significant attention. In this article, we primarily focus on the methodology of using unsaturated hydrocarbons converting into catalytic loading of organocopper intermediates under copper-hydride catalysis, instead of traditional stoichiometric amount of organometallics, to implement the addition reactions to aldehydes and ketones. This approach effectively overcomes the limitations associated with traditional methodologies. The introduction of these reactions can enrich and expand the content of nucleophilic addition knowledge in basic teaching processes, broaden students’ perspectives and thinking, facilitate their understanding of the current developments in the field, and stimulate their interest.

Key words:

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沈阳化工大学材料科学与工程学院沈阳 110142

铜氢催化不饱和烃与醛、酮的亲核加成反应

通讯作者: 熊涛, xiongt626@nenu.edu.cn

English

Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones

Corresponding author: Tao Xiong, xiongt626@nenu.edu.cn

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

铜氢催化不饱和烃与醛、酮的亲核加成反应

通讯作者: 熊涛, xiongt626@nenu.edu.cn

English

Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones

Corresponding author: Tao Xiong, xiongt626@nenu.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

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