可见光诱导的二氧化碳对活化烯烃的脱碳羧基化反应

doi:10.6023/cjoc202312018

有机化学 ›› 2024, Vol. 44 ›› Issue (5): 1675-1685.DOI: 10.6023/cjoc202312018 上一篇下一篇

研究论文

可见光诱导的二氧化碳对活化烯烃的脱碳羧基化反应

段东森, 马媛, 刘宇博, 程富, 朱道勇^*(), 王少华^*()

兰州大学药学院功能有机分子化学国家重点实验室兰州 730000

收稿日期:2023-12-18 修回日期:2023-12-21 发布日期:2024-01-05
基金资助:
国家重点研发计划(2023YFA1506404); 甘肃省科技计划(23ZDFA003); 甘肃省科技计划(23JRRA1144); 甘肃省科技计划(23JRRA1028); 甘肃省科技计划(23CXGA0043); 兰州市科技计划(2023-1-17); 兰州市科技计划(2023-QN-18); 中央高校基本科研业务专项(lzujbky-2022-ct03); 中央高校基本科研业务专项(lzujbky-2022-sp09); 中央高校基本科研业务专项(lzujbky-2023-ct02); 中央高校基本科研业务专项(lzujbky-2023-pd08); 兰州大学陇药协同创新中心和甘肃省药物研发计划(2022GSMPA0010)

Visible Light-Induced Decarbon-Carboxylation of Activated Alkenes by Carbon Dioxide

Dongsen Duan, Yuan Ma, Yubo Liu, Fu Cheng, Daoyong Zhu(), Shaohua Wang()

State Key Laboratory of Applied Organic Chemistry, School of Pharmacy, Lanzhou University, Lanzhou 730000

Received:2023-12-18 Revised:2023-12-21 Published:2024-01-05
Contact: *E-mail: wangshh@lzu.edu.cn; zhudy@lzu.edu.cn
Supported by:
National Key R&D Program of China(2023YFA1506404); Science and Technology Program of Gansu Province(23ZDFA003); Science and Technology Program of Gansu Province(23JRRA1144); Science and Technology Program of Gansu Province(23JRRA1028); Science and Technology Program of Gansu Province(23CXGA0043); Lanzhou Science and Technology Planning Project(2023-1-17); Lanzhou Science and Technology Planning Project(2023-QN-18); Fundamental Research Funds for the Central Universities(lzujbky-2022-ct03); Fundamental Research Funds for the Central Universities(lzujbky-2022-sp09); Fundamental Research Funds for the Central Universities(lzujbky-2023-ct02); Fundamental Research Funds for the Central Universities(lzujbky-2023-pd08); Collaborative Innovation Center for Northwestern Chinese Medicine of Lanzhou University and the Drug Research Project of Gansu Province(2022GSMPA0010)

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摘要/Abstract

报道了一种高效的可见光促进的活化烯烃脱碳羧化的方法, 与传统的烯烃羧化相比, 该方法条件温和, 收率最高可达96%, 对多种官能团具有很好的兼容性, 为芳基乙酸的合成及后续转化提供了新方法. 机理研究表明, 该反应是通过对烯烃碳碳双键的置换, 实现了表观碳数不变的对应羧酸的合成.

关键词: 可见光诱导, 二氧化碳, 活化烯烃, 羧基化反应

An efficient visible light-facilitated decarbon-carboxylation of activated alkenes has been successfully developed. Compared with traditional alkene carboxylation, this method features mild conditions, up to 96% yield and good compatibility with a variety of functional groups. It provides a new method for the synthesis of phenylacetic acid and its derivatives. The mechanism study shows that the reaction realizes the synthesis of the corresponding carboxylic acid with constant apparent carbon number by substituting the carbon-carbon double bond of alkene.

Key words: visible light induction, carbon dioxide, activated alkene, carboxylation

引用此文

段东森, 马媛, 刘宇博, 程富, 朱道勇, 王少华. 可见光诱导的二氧化碳对活化烯烃的脱碳羧基化反应[J]. 有机化学, 2024, 44(5): 1675-1685.

Dongsen Duan, Yuan Ma, Yubo Liu, Fu Cheng, Daoyong Zhu, Shaohua Wang. Visible Light-Induced Decarbon-Carboxylation of Activated Alkenes by Carbon Dioxide[J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1675-1685.

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图/表 7

图1. 芳基乙酸药物分子

Figure 1. Arylacetic acid drug molecules

图式1. 研究背景及本文工作

Scheme 1. Research background and this work

Entry	Photocatalyst	Amine	Solvent	Time/h	Yield^b/%
1	4DPAIPN	DIPEA	DMSO	6	58
2	4DPAIPN	TEA	DMSO	6	N.D.
3	4DPAIPN	Cy₂NMe	DMSO	6	73
4	4DPAIPN	NIMBA	DMSO	6	75
5^c	4DPAIPN	NIMBA	DMSO	6	30
6^d	4DPAIPN	NIMBA	DMSO	6	65
7	4DPAIPN	NIMBA	DMF	6	69
8	4DPAIPN	NIMBA	NMP	6	45
9	4DPAIPN	NIMBA	MeCN	6	52
10	4CzIPN	NIMBA	DMSO	6	N.D.
11	3DPAFIPN	NIMBA	DMSO	6	70
12	fac-Ir(ppy)₃	NIMBA	DMSO	6	N.D.
13	4DPAIPN	NIMBA	DMSO	1	58
14	4DPAIPN	NIMBA	DMSO	3	70
15	4DPAIPN	NIMBA	DMSO	12	75
16	4DPAIPN	NIMBA	DMSO	24	86 (78)^e

表1. 反应条件的优化a

Table 1. Optimization of reaction conditions

图2. 脱碳羧基化反应的底物范围

Figure 2. Substrate scope of decarbon-carboxylation

图3. 合成的药物分子

Figure 3. Synthesis of drug moleculars

图式2. 控制实验

Scheme 2. Control experiments

图式3. 可能的机理

Scheme 3. Possible mechanism

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可见光诱导的二氧化碳对活化烯烃的脱碳羧基化反应

Visible Light-Induced Decarbon-Carboxylation of Activated Alkenes by Carbon Dioxide

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