可见光氧化还原钴催化立体发散性合成1,4-二烯

doi:10.1016/S1872-2067(24)60031-8

催化学报 ›› 2024, Vol. 61: 291-300.DOI: 10.1016/S1872-2067(24)60031-8

可见光氧化还原钴催化立体发散性合成1,4-二烯

任行宇^a^,^b, 刘佳俊^a, 张士启^b, 李彦霖^b, 崔坤^b, 李静^a^,^*(), 顾正洋^a^,^b^,^*(), 夏纪宝^b^,^c^,^*()

^a盐城工学院化学化工学院和纺织服装学院, 江苏盐城 224003
^b中国科学院兰州化学物理研究所, 羰基合成与选择氧化国家重点实验室, 甘肃兰州 730000
^c杭州师范大学材料化学与化工学院, 教育部有机硅化学与材料技术重点实验室, 浙江杭州 311121

收稿日期:2024-02-02 接受日期:2024-03-24 出版日期:2024-06-18 发布日期:2024-06-20
通讯作者: * 电子信箱: jli@ycit.edu.cn (李静), zhengyang.gu@qq.com (顾正洋), jibaoxia@licp.cas.cn (夏纪宝).
基金资助:
国家自然科学基金(22271296);国家自然科学基金(22001226);国家自然科学基金(22276161);江苏省自然科学基金(BK20201193);江苏省自然科学基金(BK20201473);江苏省高等学校自然科学基金项目(20KJB150016);兰州化学物理研究所重大计划项目(ZYFZFX-1);江苏省青蓝工程

Photoredox cobalt-catalyzed stereodivergent synthesis of 1,4-dienes

Xing-Yu Ren^a^,^b, Jia-Jun Liu^a, Shi-Qi Zhang^b, Yan-Lin Li^b, Kun Cui^b, Jing Li^a^,^*(), Zheng-Yang Gu^a^,^b^,^*(), Ji-Bao Xia^b^,^c^,^*()

^aSchool of Chemistry and Chemical Engineering & College of Textiles and Clothing, Yancheng Institute of Technology, Yancheng 224003, Jiangsu, China
^bState Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), University of Chinese Academy of Sciences, Chinese Academy of Sciences, Lanzhou 730000, Gansu, China
^cCollege of Material Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou 311121, Zhejiang, China

Received:2024-02-02 Accepted:2024-03-24 Online:2024-06-18 Published:2024-06-20
Contact: * E-mail: jli@ycit.edu.cn (J. Li), zhengyang.gu@qq.com (Z.-Y. Gu), jibaoxia@licp.cas.cn (J.-B. Xia).
Supported by:
National Natural Science Foundation of China(22271296);National Natural Science Foundation of China(22001226);National Natural Science Foundation of China(22276161);Natural Science Foundation of Jiangsu Province(BK20201193);Natural Science Foundation of Jiangsu Province(BK20201473);Natural Science Foundation of the Jiangsu Higher Education Institutions of China(20KJB150016);Major Program of the Lanzhou Institute of Chemical Physics(ZYFZFX-1);Qinglan Project of Jiangsu Province

摘要/Abstract

摘要：

1,4-二烯是一类重要的烯烃化合物, 其分子骨架广泛存在于药物和天然产物中. 由于1,4-二烯分子在有机合成中具有重要作用, 目前其合成方法已被广泛研究, 包括1,3-二烯的氢烯基化、炔烃的氢烯丙基化、乙烯基和烯丙基试剂的交叉偶联等. 然而, 由于1,4-二烯的热力学稳定性, 现有的合成方法主要倾向于生成E-立体选择性的产物, 而Z-异构体的生成则相对困难. 值得注意的是, 通过同一组底物同时构建1,4-二烯的Z和E异构体的立体发散性合成策略鲜有报道. 因此, 发展新型催化体系, 以同时构建1,4-二烯的Z和E异构体具有十分重要的意义和应用前景.
本文报道了一种高效的可见光光致氧化还原/钴协同催化策略, 该策略以联烯与炔烃为原料, 通过调控反应溶剂即可实现立体发散性地构建Z,E-和E,E-1,4-二烯化合物. 该反应在室温下, 以2,4,5,6-四(9-咔唑基)-间苯二腈(4CzIPN)作为光敏剂, 4,6-双(二苯基膦基)-10H-吩噁嗪为配体, H₂O和DIPEA作为氢源, 实现了1,4-二烯的高效合成. 值得一提的是, 通过简单地调控溶剂可以直接控制产物的立体选择性, 即以乙腈为溶剂时可得到Z,E-1,4-二烯产物, 而使用2-MeTHF作为溶剂时, 则得到E,E-1,4-二烯产物. 此外, 该反应对炔烃底物具有良好的兼容性, 包括乙基、硅醚、羟基和环丙基等非对称的芳基烷基内炔, 均能与联烯有效偶联, 以较高收率得到目标产物. 此外, 芳基上带有各种富电子和缺电子基团的炔烃也能很好地参与反应. 联烯底物研究结果表明, 联烯上的酯基对反应效率有显著影响, 具有较小酯取代基的联烯, 如甲基和乙基, 反应活性较低, 相应的产物收率较低; 而具有较大酯基的联烯, 如异丙基、苄基和叔丁基, 则能获得更高的产率. 此外, 当使用苯基、酸酐、二苯基氧化膦或磺酰基等其他官能团取代的联烯时, 反应无法发生. 通过氘代实验、荧光猝灭实验等一系列控制实验以及密度泛函理论计算, 揭示了该反应机制. 反应过程涉及五元钴环戊烯中间体的分解, 并通过光催化的能量转移过程实现了E,E-1,4-二烯的E→Z异构化, 最终实现Z,E-1,4-二烯的立体选择性合成.
综上所述, 本文提出了一种新的钴催化炔烃-联烯的选择性还原偶联反应. 通过结合可见光光致氧化还原与钴协同催化策略, 在温和的条件下, 以H₂O和DIPEA作为氢源, 实现了具有良好区域选择性和立体选择性的Z,E-和E,E-1,4-二烯的立体发散性合成. 通过控制反应溶剂来实现立体选择性, 本研究为立体发散性合成1,4-二烯化合物提供了一种简单有效的新途径.

关键词: 1,4-二烯, 钴催化, 光氧化还原, 还原偶联, 炔烃, 联烯

Abstract:

1,4-Dienes are important scaffolds widely used in natural products and medicinal compounds. Herein, we report a highly efficient method for the straightforward synthesis of 1,4-dienes via regio- and stereoselective reductive coupling of alkynes and allenes, catalyzed by visible-light photoredox cobalt. In contrast to the conventional E-alkene products, both (Z,E)- and (E,E)-1,4-dienes were synthesized with good regio- and stereoselectivities under mild conditions. In this photoredox reaction, Hünig’s base and water were utilized as hydrogen sources instead of the commonly used Hantzsch esters. The mechanistic and density functional theory studies indicate that the reaction undergoes protolysis of a cobaltacyclopentene intermediate and photocatalytic E→Z isomerization of (E,E)-1,4-dienes to (Z,E)-1,4-dienes via an energy transfer process.

Key words: 1,4-Dienes, Cobalt catalysis, Photoredox, Reductive coupling, Alkynes, Allenes

任行宇, 刘佳俊, 张士启, 李彦霖, 崔坤, 李静, 顾正洋, 夏纪宝. 可见光氧化还原钴催化立体发散性合成1,4-二烯[J]. 催化学报, 2024, 61: 291-300.

Xing-Yu Ren, Jia-Jun Liu, Shi-Qi Zhang, Yan-Lin Li, Kun Cui, Jing Li, Zheng-Yang Gu, Ji-Bao Xia. Photoredox cobalt-catalyzed stereodivergent synthesis of 1,4-dienes[J]. Chinese Journal of Catalysis, 2024, 61: 291-300.

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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(24)60031-8

https://www.cjcatal.com/CN/Y2024/V61/I6/291

图/表 6

Fig. 1. Selective synthesis of 1,4-dienes. (A) Bioactive natural products containing 1,4-diene motifs. (B) Catalytic reactions for the synthesis of 1,4-dienes. X: H or halogen group. (C) Photosensitizer-controlled stereodivergent synthesis of 1,4-dienes. HE: Hantzsch esters. (D) This work: Solvent-controlled stereodivergent synthesis of 1,4-dienes.

Table 1 Summary of the effects of reaction parameters on the reaction efficiency a.

Entry	Co catalysis	Ligand	Solvent	Yield of 3 ^b (%)	Yield of 4 ^b (%)
1	Co(acac)₂	Xantphos	MeCN	21	<2
2	CoBr₂	Xantphos	MeCN	25	<2
3	CoCl₂	Xantphos	MeCN	20	<2
4	Co(OAc)₂	Xantphos	MeCN	55	<2
5	Co(OAc)₂	DPPP	MeCN	<2	<2
6	Co(OAc)₂	DPPE	MeCN	<2	<2
7	Co(OAc)₂	Nixantphos	MeCN	67	<2
8	Co(OAc)₂	Nixantphos	THF	12	36
9	Co(OAc)₂	Nixantphos	2-MeTHF	17	45
10^c	Co(OAc)₂	Nixantphos	2-MeTHF	19	55
11	Co(OAc)₂	Nixantphos	1,4-Dioxane	<2	<2
12	Co(OAc)₂	Nixantphos	MeOH	8	<2
13^d	Co(OAc)₂	Nixantphos	MeCN	75	<2

Fig. 2. Reaction scope of 1,4-dienes. All reactions were performed with alkynes (0.2 mmol) and allenes (0.4 mmol) in MeCN (2 mL) to obtain the isolated products. The rr ratio stands for the reaction major coupling at β-position of alkynes. The stereochemistry of the product was confirmed by 1H-1H NOESY analysis of 5 and 22.

Fig. 3. Reaction scope of 1,4-dienes and transformations. (A) Examples of (E,E)-1,4-dienes. All reactions were performed with alkynes (0.2 mmol) and allenes (0.6 mmol) in 2-MeTHF (2 mL); isolated yield of product is provided. The stereochemistry of the product was confirmed by 1H-1H NOESY analysis of 33. aCrude E/Z ratio was determined by GC-MS analysis. (B) Reaction of butynoate with allene 2. (C) Scale-up of alkynes 1 and 2. (D) Hydrolysis of ester groups into acidic groups.

Fig. 4. Control experiments and mechanistic studies. (A) Control reaction without H2O. (B) Deuterium-labeling experiments using D2O. (C) Effect of ester group. (D) Visible light-induced isomerization of alkene. (E) Triplet-state energies affected by solvents. (F) DFT studies of the free energies of the key intermediates. All the calculations were performed at the M06-L/6-31G(d)/SDD (for Co)/pcm (THF or MeCN) level of theory. Free energies are expressed in kcal mol?1.

Fig. 5. Proposed reaction mechanism.

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可见光氧化还原钴催化立体发散性合成1,4-二烯

Photoredox cobalt-catalyzed stereodivergent synthesis of 1,4-dienes

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