可见光催化CO2参与的芳基烯烃碳碳双键断键羧基化反应

doi:10.1016/S1872-2067(23)64583-8

催化学报 ›› 2024, Vol. 56: 74-80.DOI: 10.1016/S1872-2067(23)64583-8

可见光催化CO₂参与的芳基烯烃碳碳双键断键羧基化反应

曹可弓^a^,¹, 高田宇^a^,¹, 廖黎丽^b^,^*(), 冉川昆^a, 蒋元旭^a, 章炜^c, 周琦^a, 叶剑衡^a, 蓝宇^b^,^d, 余达刚^a^,^e^,^*()

^a四川大学化学学院, 绿色化学与技术教育部重点实验室, 四川成都610064
^b重庆大学化学化工学院, 理论与计算化学重庆市重点实验室, 重庆400044
^c四川大学华西公共卫生学院, 华西第四医院, 四川成都610041
^d郑州大学化学学院, 绿色催化中心, 河南郑州450001
^e南开大学元素有机化学国家重点实验室, 天津300071

收稿日期:2023-12-10 接受日期:2023-12-13 出版日期:2024-01-18 发布日期:2024-01-10
通讯作者: *电子信箱: liaoll@cqu.edu.cn (廖黎丽), dgyu@scu.edu.cn (余达刚).
作者简介:¹共同第一作者.
基金资助:
国家自然科学基金(22225106);国家自然科学基金(22201027);国家自然科学基金(22101191);四川大学基础研究基金(2020SCUNL102);中国博士后面上基金(2021M700578);中央高校基本科研业务费.

Photocatalytic carboxylation of styrenes with CO₂ via C=C double bond cleavage

Ke-Gong Cao^a^,¹, Tian-Yu Gao^a^,¹, Li-Li Liao^b^,^*(), Chuan-Kun Ran^a, Yuan-Xu Jiang^a, Wei Zhang^c, Qi Zhou^a, Jian-Heng Ye^a, Yu Lan^b^,^d, Da-Gang Yu^a^,^e^,^*()

^aKey Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, Sichuan, China
^bChongqing Key Laboratory of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400044, China
^cWest China School of Public Health and West China Fourth Hospital, Sichuan University, Chengdu 610041, Sichuan, China
^dInstitute of Green Catalysis, College of Chemistry, Zhengzhou University, Zhengzhou 450001, Henan, China
^eState Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China

Received:2023-12-10 Accepted:2023-12-13 Online:2024-01-18 Published:2024-01-10
Contact: *E-mail: liaoll@cqu.edu.cn (L.-L. Liao), dgyu@scu.edu.cn (D.-G. Yu).
About author:¹Contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22225106);National Natural Science Foundation of China(22201027);National Natural Science Foundation of China(22101191);Fundamental Research Funds from Sichuan University(2020SCUNL102);Postdoctoral Science Foundation of China(2021M700578);Fundamental Research Funds for the Central Universities.

摘要/Abstract

摘要：

烯烃广泛存在于自然界中, 在医药、农药和材料等领域具有重要应用. 烯烃的C=C键断裂和转化是许多工业过程的基础, 可以实现烃类资源的重组与利用. 目前, C=C键参与的氧化裂解和烯烃复分解反应已有广泛的研究. 相比而言, C=C键参与的还原裂解虽然是烯烃与一系列亲电试剂反应合成功能分子的重要途径, 但受限于烯烃自身结构和反应特点, 该过程存在较大的挑战, 目前研究很少. CO₂具有储量丰富、廉价易得、无毒且可循环再生等优点, 是合成多种大宗化学品及精细化学品的理想碳一资源. 然而, CO₂由于热力学稳定性及动力学惰性, 在温和条件下难以高效、高选择性转化. 因此, 利用CO₂参与烯烃C=C键还原裂解, 选择性构建高值化合物, 是一个重要且具有挑战性的研究方向.

近年来, 可见光催化由于具有反应条件温和、官能团兼容性高等优点, 为有机合成等领域提供了新的发展机遇. 本文利用二环己基甲基胺作为电子给体, 成功实现了可见光催化CO₂参与的芳基烯烃C=C键断键羧基化反应. 该反应成功的关键在于, 二环己基甲基胺既能高效还原淬灭激发态光敏剂并参与烯烃的胺基烷基-羧基化反应, 又不明显抑制胺基烷基化中间体对激发态光敏剂的还原淬灭. 研究结果表明, 多种不同取代(如给电子基和吸电子基)的芳基烯烃均可与CO₂发生羧基化反应, 高效高选择性地构建了一系列官能团丰富的芳基乙酸类化合物(如萘普生等药物分子). 该方法具有反应条件温和(1 atm, 室温)、官能团耐受性好以及可用于合成药物衍生物等特点. 此外, 本文通过氘代实验等机理研究和密度泛函理论计算证明, 胺甲基羧化中间体、苄基自由基和苄基碳负离子都是该反应的关键中间体, 并提出了可能的反应机理: 首先, 二环己基甲基胺还原淬灭激发态光敏剂, 产生α-胺基碳自由基, 与芳基烯烃发生自由基加成反应, 得到苄基自由基, 进而被还原态光敏剂还原为碳负离子, 对CO₂亲核进攻得到烯烃的胺基烷基-羧基化中间体; 作为电子给体, 该中间体可以淬灭另一分子的激发态光敏剂, 并通过分子内去质子化过程, 产生α-胺基碳自由基物种, 进而经历自由基型β-C断裂, 生成热力学更稳定的羧基化苄基自由基, 从而实现了烯烃C=C键的还原裂解; 最后, 新产生的苄基自由基被进一步还原为碳负离子, 经历质子化过程后得到目标产物.

综上, 本文以还原裂解的方式丰富了C=C键断键官能团化反应领域, 在温和条件下实现了CO₂的高效高选择性转化, 合成了高附加值的芳基乙酸类化合物, 阐明了反应机制, 为烯烃和CO₂的同时高值化利用提供了新思路, 为后续相关反应的开发和应用提供参考.

关键词: 二氧化碳, 可见光催化, C=C键裂解, 羧基化, 芳基乙酸

Abstract:

Catalytic cleavage of C=C double bonds in alkenes is highly important to convert feedstocks into high-value compounds. However, these approaches are mainly limited to oxidative cleavage of alkenes with excess oxidants and redox-neutral alkene metathesis. In contrast, reductive C=C double bond cleavage and functionalization have not been reported. Herein, we report a novel visible-light photoredox-catalyzed carboxylation of styrenes with CO₂ via reductive C=C double bond cleavage. The use of dicyclohexylmethylamine as scission reagent is the key to the success. Different from previous homologation reactions with CO₂, this protocol enabled exchange of the carbon of styrenes with CO₂, affording important aryl acetic acids via C=C double bond cleavage. Moreover, preliminary mechanistic investigation and DFT calculations shed light on the reaction mechanism, disclosing aminomethyl-carboxylation intermediate, benzylic radicals and carbanions as key intermediates in the reaction.

Key words: Carbon dioxide, Visible-light photoredox catalysis, C=C bond cleavage, Carboxylation, Aryl acetic acids

曹可弓, 高田宇, 廖黎丽, 冉川昆, 蒋元旭, 章炜, 周琦, 叶剑衡, 蓝宇, 余达刚. 可见光催化CO₂参与的芳基烯烃碳碳双键断键羧基化反应[J]. 催化学报, 2024, 56: 74-80.

Ke-Gong Cao, Tian-Yu Gao, Li-Li Liao, Chuan-Kun Ran, Yuan-Xu Jiang, Wei Zhang, Qi Zhou, Jian-Heng Ye, Yu Lan, Da-Gang Yu. Photocatalytic carboxylation of styrenes with CO₂ via C=C double bond cleavage[J]. Chinese Journal of Catalysis, 2024, 56: 74-80.

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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(23)64583-8

https://www.cjcatal.com/CN/Y2024/V56/I1/74

图/表 7

Fig. 1. Visible-light photoredox-catalyzed carboxylation with CO2 via reductive cleavage of C=C bond in styrenes.

Table 1 Optimization of reaction conditions.a


Entry	Variations	2a ^b (%)
1	none	91 (88)
2	DIPEA instead of Cy₂NMe	47
3	Et₃N instead of Cy₂NMe	17
4 5	4CzIPN instead of 3DPA2FBN 4DPAIPN instead of 3DPA2FBN	8 74
6	fac-Ir(ppy)₃ instead of 3DPA2FBN	2
7	KOMe instead of HCOOK	74
8	K₂CO₃ instead of HCOOK	71
9	DMSO instead of DMAc	72
10	NMP instead of DMAc	70
11	w/o CO₂	N. D.
12	w/o 3DPA2FBN	N. D.
13	w/o Cy₂NMe	N. D.
14	w/o Light	N. D.
15	w/o HCOOK	78

Table 2 Substrate scope of 1,1-diarylalkenes a.

Table 3 Substrate scope of mono-aryl-substituted alkenes a.

Scheme 1. Mechanistic studies.

Scheme 2. Calculated free energy profiles. Profiles of transformation of carbon-carboxylated intermediate. The values given in kcal/mol are the relative free energies calculated by the M06/6-311+G(d,p)//B3LYP/6-31+G(d) method in DMAc solvent.

Scheme 3. Possible mechanism.

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可见光催化CO₂参与的芳基烯烃碳碳双键断键羧基化反应

Photocatalytic carboxylation of styrenes with CO₂ via C=C double bond cleavage

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