多相铁催化环状醚C(sp3)—H键活化的芳基烯烃氧烷基化

doi:10.6023/cjoc202312021

有机化学 ›› 2024, Vol. 44 ›› Issue (6): 1978-1986.DOI: 10.6023/cjoc202312021 上一篇下一篇

研究论文

多相铁催化环状醚C(sp³)—H键活化的芳基烯烃氧烷基化

于蕾^a, 盛康^b, 李亭^a^,^*(), 唐从辉^b^,^*()

a 南阳师范学院化学与制药工程学院河南南阳 473061
b 华中科技大学化学与化工学院能量转换与存储材料化学教育部重点实验室材料化学与服役失效湖北省重点实验室武汉 430074

收稿日期:2023-12-22 修回日期:2024-02-01 发布日期:2024-02-27
基金资助:
国家自然科学基金(22371083); 国家自然科学基金(22001086)

Heterogeneous Iron-Catalyzed Oxyalkylation of Vinylarenes via C(sp³)—H Activation of Cyclic Ethers

Lei Yu^a, Kang Sheng^b, Ting Li^a,*(), Conghui Tang^b,*()

a College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang, Henan 473061
b Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Material Chemistry and Service Failure, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan 430074

Received:2023-12-22 Revised:2024-02-01 Published:2024-02-27
Contact: * E-mail: chemlt2015@nynu.edu.cn; ctang@hust.edu.cn
Supported by:
National Natural Science Foundation of China(22371083); National Natural Science Foundation of China(22001086)

文章分享

1. 241978S.pdf.pdf(1357KB)

摘要/Abstract

烯烃双官能团化是一种重要的在双键上构建新的化学键的方法, 烯烃的氧烷基化反应能够提供同时生成含有碳碳键和碳氧键的产物, 然而当前的氧烷基化方法需要使用过氧叔丁醇作为氧化剂. 因此亟需发展一类需氧氧化体系的氧烷基化反应. 报道了一例温和条件下多相铁催化的苯乙烯及其衍生物的氧烷基化反应, 使用空气作为氧化剂和氧源, 并进行了详细的催化剂表征、底物范围探索以及机理实验, 且给出了可能的机理过程.

关键词: 烯烃, 双官能团化, sp³碳氢键活化, 多相铁催化

Alkene difunctionalization is an important route to construct new chemical bonds over the olefin double bond, oxyalkylation reaction of olefins will provide C—C bond and C—O bond forming products. The current oxyalkylation methods rely in employing tert-butyl hydroperoxide as the oxidant. Therefore, developing an aerobic oxidation system for this transformation is highly desired. Herein, an unprecedented heterogeneous iron catalyzed oxyalkylation of styrene derivatives under mild conditions was reported, using air as oxidant and oxygen source. Detailed catalyst characterization, substrate scope and mechanistic studies were carried out and a proposed mechanism was given.

Key words: alkene, difunctionalization, C(sp³)—H activation, heterogeneous iron catalysis

引用此文

于蕾, 盛康, 李亭, 唐从辉. 多相铁催化环状醚C(sp³)—H键活化的芳基烯烃氧烷基化[J]. 有机化学, 2024, 44(6): 1978-1986.

Lei Yu, Kang Sheng, Ting Li, Conghui Tang. Heterogeneous Iron-Catalyzed Oxyalkylation of Vinylarenes via C(sp³)—H Activation of Cyclic Ethers[J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1978-1986.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 7

Scheme 1. Transition metal-catalyzed alkene oxyalkylation reactions

Figure 1. Characterizations of Fe@Fe3O4-N/C

Table 1. Reaction conditions optimizationa

Table 2. Substrate scope of vinylarenesa

Table 3. Substrate scope of cyclic ethersa

Scheme 2. Mechanistic studies and control experiments

Scheme 3. Proposed mechanism of oxyalkylation reaction of vinylarenes

参考文献 17

[1]	(a) Yang, X.; Liu, X.; Wang, L. Chin. J. Org. Chem. 2023, 43, 914. (in Chinese)
	(杨幸, 刘旭, 王丽佳, 有机化学, 2023, 43, 914.)
	(b) Zhang, B.; Guan, H.; Liu, B.; Shi, B. Chin. J. Org. Chem. 2014, 34, 1487. (in Chinese)
	(张博, 管晗曦, 刘斌, 史炳锋, 有机化学, 2014, 34, 1487.)
	(c) Li, B.-J.; Shi, Z.-J. Chem. Soc. Rev. 2012, 41, 5588.
	(d) Zhang, T.; Wu, Y.-H.; Wang, N.-X.; Xing, Y. Synthesis 2019, 51, 4531.
[2]	(a) Xu, L.; Wang, F.; Chen, F.; Zhu, S.; Chu, L. Chin. J. Org. Chem. 2022, 42, 1. (in Chinese)
	(徐磊, 王方, 陈凡, 朱圣卿, 储玲玲, 有机化学, 2022, 42, 1.)
	(b) Fu, X.; Zhao, W. Chin. J. Org. Chem. 2019, 39, 625. (in Chinese)
	(付晓飞, 赵文献, 有机化学, 2019, 39, 625.)
	(c) Derosa, J.; Apolinar, O.; Kang, T.; Tran, V. T.; Engle, K. M. Chem. Sci. 2020, 11, 4287.
	(d) Yin, G.; Mu, X.; Liu, G. Acc. Chem. Res. 2016, 49, 2413.
	(e) Liu, J; Wan, J; Liu, Y. Org. Chem. Front., 2024, 11, 597.
	(f) Ye, J; Liu, Y; Luo, J; Wan, J. Org. Lett. 2023, 25, 8451.
[3]	(a) Gandeepan, P; Müller, T; Zell, D; Cera, G; Warratz, S; Ackermann, L. Chem. Rev. 2019, 119, 2192.
	(b) Docherty, J; Lister, T; Mcarthur, G; Findlay, M; Domingo-Legarda, P; Kenyon, J; Choudhary, S; Larrosa, I. Chem. Rev. 2023, 123, 7692.
[4]	Cheng, K.; Huang, L.; Zhang, Y. Org. Lett. 2009, 11, 2908.
[5]	Li, J.; Li, J.; Yuan, S.; Zhang, Q.; Li, D. Asian J. Org. Chem. 2019, 8, 1842.
[6]	Kibriya, G.; Ghosh, D.; Hajra, A. Sci. China Chem. 2020, 63, 42.
[7]	Kim, J. Y.; Park, J. C.; Song, H.; Park, K. H. Bull. Korean Chem. Soc. 2010, 31, 3509.
[8]	Sun, H.; Zhang, Y.; Guo, F.; Zha, Z.; Wang, Z. J. Org. Chem. 2012, 77, 3563.
[9]	(a) Bauer, I.; Knoelker, H.-J. Chem. Rev. 2015, 115, 3170.
	(b) Fuerstner, A. ACS Cent. Sci. 2016, 2, 778.
	(c) Shang, R.; Ilies, L.; Nakamura, E. Chem. Rev. 2017, 117, 9086.
[10]	(a) Chen, S.; Xue, W.; Tang, C. ChemSusChem 2022, 15, e202201522.
	(b) Sun, F.; Huang, J.; Wei, Z.; Tang, C.; Liu, W. Angew. Chem., Int. Ed. 2023, 62, e202303433.
	(c) Tang, C.; Jiao, N. J. Am. Chem. Soc. 2012, 134, 18924.
	(d) Tang, C.; Jiao, N. Angew. Chem., Int. Ed. 2014, 53, 6528.
	(e) Tang, C.; Surkus, A.-E.; Chen, F.; Pohl, M.-M.; Agostini, G.; Schneider, M.; Junge, H.; Beller, M. Angew. Chem., Int. Ed. 2017, 56, 16616.
	(f) Tian, H.; Xue, W.; Wu, J.; Yang, Z.; Lu, H.; Tang, C. Org. Chem. Front. 2022, 9, 4554.
	(g) Xue, W.; Jiang, Y.; Lu, H.; You, B.; Wang, X.; Tang, C. Angew. Chem., Int. Ed. 2023, 62, e202314364.
	(h) Xue, W.; Tang, C. Energies 2022, 15, 2011.
	(i) Xue, W.; Zhu, Z.; Chen, S.; You, B.; Tang, C. J. Am. Chem. Soc. 2023, 145, 4142.
	(j) Zhu, B.; Qu, L.; Tang, C. Chin. J. Org. Chem. 2023, 43, 1211. (in Chinese)
	(朱保颖, 屈凌波, 唐从辉, 有机化学, 2023, 43, 1211.)
	(k) Zhu, M.; Tian, H.; Chen, S.; Xue, W.; Wang, Y.; Lu, H.; Li, T.; Chen, F.; Tang, C. J. Catal. 2022, 416, 170.
[11]	Jiang, Y.; Chen, S.; Chen, Y.; Gu, A.; Tang, C. J. Am. Chem. Soc. 2024, 146, 2769.
[12]	Tang, C.; Qiu, X.; Cheng, Z.; Jiao, N. Chem. Soc. Rev. 2021, 50, 8067.
[13]	Cui, X.; Li, Y.; Bachmann, S.; Beller, M. J. Am. Chem. Soc. 2015, 137, 10652.
[14]	(a) Formenti, D.; Topf, C.; Junge, K.; Ragaini, F.; Beller, M. Catal. Sci. Technol. 2016, 6, 4473.
	(b) Jagadeesh, R. V.; Junge, H.; Beller, M. Nat. Commun. 2014, 5, 4123.
	(c) Sarkar, A.; Formenti, D.; Ferretti, F.; Kreyenschulte, C.; Bartling, S.; Junge, K.; Beller, M.; Ragaini, F. Chem. Sci. 2020, 11, 6217.
[15]	(a) Zhao, B; Yin, X; Li, H; Cheng, K; Wan, J. Org. Chem. Front. 2023, 10, 1942.
	(b) Zeng, J; Wan, J; Liu, Y. J. Org. Chem. 2022, 87, 13195.
[16]	Kuga, T; Sasano, Y; Iwabuchi, Y. Chem. Commun. 2018, 54, 798.
[17]	Chen, R; Wang, K; Wang, Z; Ma, X; Wang, D; Zhang, A; Liu, L. ChemistrySelect 2020, 5, 2078.

多相铁催化环状醚C(sp³)—H键活化的芳基烯烃氧烷基化

Heterogeneous Iron-Catalyzed Oxyalkylation of Vinylarenes via C(sp³)—H Activation of Cyclic Ethers

RichHTML

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

图/表 7

参考文献 17

相关文章 15

编辑推荐

相关统计

本文评价

[1]	陆玲依, 邱晓东. 自由基形式烯烃双烷基化反应研究进展[J]. 有机化学, 2024, 44(6): 1701-1718.
[2]	史会兵, 王耀伟, 王鹏, 赵德明, 冯保林, 晏耀宗, 杨桂爱. 羰基化反应在大宗化学品以及精细化学品合成中的应用[J]. 有机化学, 2024, 44(6): 1811-1830.
[3]	孙超, 周泉, 李传莹, 王磊. 苯并唑-氮杂环卡宾钯配合物的合成表征及应用[J]. 有机化学, 2024, 44(6): 1957-1966.
[4]	曹香雪, 贾雅会, 殷世纪, 徐亮, 韦玉, 宋欢欢. 可见光诱导二氢喹唑啉酮碳碳键断裂与三氟甲基取代烯烃的脱氟烷基化反应研究[J]. 有机化学, 2024, 44(5): 1549-1557.
[5]	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.
[6]	晏宇轩, 陆晚晴, 钱慧俊, 吕雷阳, 李志平. 钯催化偕二氟环丙烷开环与1,3-二羰基化合物的单/双氟烯丙基化反应[J]. 有机化学, 2024, 44(5): 1630-1640.
[7]	张剑, 梁万洁, 杨艺, 闫法超, 刘会. 联烯胺化合物的区域选择性双官能团化[J]. 有机化学, 2024, 44(2): 335-348.
[8]	李思达, 崔鑫, 舒兴中, 吴立朋. 钛催化的烯烃制备1,1-二硼化合物[J]. 有机化学, 2024, 44(2): 631-637.
[9]	张建涛, 张聪, 莫诺琳, 罗佳婷, 陈莲芬, 刘卫兵. 氯仿参与的烯烃自由基加成反应的研究进展[J]. 有机化学, 2023, 43(9): 3098-3106.
[10]	卢凯, 屈浩琦, 陈樨, 秋慧, 郑晶, 马猛涛. 无催化剂、无溶剂条件下炔烃和烯烃与儿茶酚硼烷的硼氢化反应[J]. 有机化学, 2023, 43(6): 2197-2205.
[11]	陆晓雨, 孙晓梅, 钮亚琴, 王俊超, 殷文婧, 高梦婷, 刘孜, 韦正桓, 陶庭骅. 铜催化氟代丙烯酸与氧杂吖丙啶的脱羧交叉偶联反应[J]. 有机化学, 2023, 43(6): 2110-2119.
[12]	李思达, 舒兴中, 吴立朋. 锆、钛介导的烯烃、炔烃硼氢化[J]. 有机化学, 2023, 43(5): 1751-1760.
[13]	高师泉, 刘闯军, 杨俊锋, 张俊良. 钴催化的烯烃和炔烃的电化学还原偶联反应[J]. 有机化学, 2023, 43(4): 1559-1565.
[14]	梁志鹏, 叶浩, 张海滨, 姜国民, 吴新星. 环丁酮类腙参与的偕二氟环丙烷开环胺化反应[J]. 有机化学, 2023, 43(4): 1483-1491.
[15]	张妍妍, 张珠珠, 朱圣卿, 储玲玲. 镍催化不对称酰基化反应研究进展[J]. 有机化学, 2023, 43(3): 1023-1035.