中心手性金属铑配合物催化的不对称光诱导Giese自由基加成反应

doi:10.6023/cjoc202004041

有机化学 ›› 2020, Vol. 40 ›› Issue (11): 3944-3952.DOI: 10.6023/cjoc202004041 上一篇下一篇

所属专题：有机光催化虚拟合辑；创刊四十周年专辑

研究论文

中心手性金属铑配合物催化的不对称光诱导Giese自由基加成反应

陈亮^a,b, 胡良建^a,c, 杜宇^a, 苏伟平^a, 康强^a

a 中国科学院福建物质结构研究所结构化学国家重点实验室福州 350002;
b 中国科学院大学北京 100049;
c 福建农林大学材料工程学院福州 350002

收稿日期:2020-04-25 修回日期:2020-05-14 发布日期:2020-05-20
通讯作者: 苏伟平, 康强 E-mail:wpsu@fjirsm.ac.cn,kangq@fjirsm.ac.cn
基金资助:
国家自然科学基金面上（No.21871261）资助项目.

Asymmetric Photoinduced Giese Radical Addition Enabled by a Single Chiral-at-Metal Rhodium Complex

Chen Liang^a,b, Hu Liangjian^a,c, Du Yu^a, Su Weiping^a, Kang Qiang^a

a State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002;
b University of Chinese Academy of Sciences, Beijing 100049;
c College of Material Engineering, Fujian Agriculture and Forestry University, Fuzhou 350002

Received:2020-04-25 Revised:2020-05-14 Published:2020-05-20
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21871261).

文章分享

1. cjoc202004041辅助材料.pdf(2070KB)

摘要/Abstract

报道了一种可见光驱动的双功能中心手性金属铑配合物催化的不对称自由基加成反应，由对胺基苯乙酸生成的对胺基苄基自由基对α，β-不饱和酰基咪唑进行立体选择性的1，4-加成，以中高收率和高对映选择性合成了一系列加成产物.该反应具有对映选择性高、反应条件温和、操作简单等特点.根据对双功能中心手性金属配合物催化的研究和文献报道，提出了一个合理的反应机理.

关键词: 可见光催化, 双功能手性铑配合物, Giese自由基加成反应, 对胺基苄基自由基

A visible-light driven asymmetric Giese radical addition catalyzed by a bifunctional chiral-at-metal rhodium complex has been developed. para-Aminobenzyl radicals generated from para-aminophenylacetic acids could undergo a 1,4-addition in a highly enantioselective approach to α,β-unsaturated 2-acyl imidazoles, and a variety of corresponding adducts were obtained in moderate to high yields with excellent enantioselectivities. This reaction features high enantioselectivity, mild reaction conditions and an operationally simple procedure. A plausible reaction mechanism is proposed based on our research and literature precedents on dual functional chiral-at-metal catalysis.

Key words: visible-light photoredox catalysis, bifunctional chiral-at-metal rhodium complex, Giese radical addition, para-aminobenzyl radical

引用此文

陈亮, 胡良建, 杜宇, 苏伟平, 康强. 中心手性金属铑配合物催化的不对称光诱导Giese自由基加成反应[J]. 有机化学, 2020, 40(11): 3944-3952.

Chen Liang, Hu Liangjian, Du Yu, Su Weiping, Kang Qiang. Asymmetric Photoinduced Giese Radical Addition Enabled by a Single Chiral-at-Metal Rhodium Complex[J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3944-3952.

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

分享此文

参考文献

[1] For selected reviews on visible-light photoredox catalysis, see:(a) Xuan, J.; Xiao, W. J. Angew. Chem., Int. Ed. 2012, 51, 6828.
(b) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
(c) Douglas, J. J.; Sevrin, M. J.; Stephenson, C. R. J. Org. Process Res. Dev. 2016, 20, 1134.
(d) Gentry, E. C.; Knowles, R. R. Acc. Chem. Res. 2016, 49, 1546.
(e) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075.
(f) Shaw, M. H.; Twilton, J.; MacMillan, D. W. C. J. Org. Chem. 2016, 81, 6898.
(g) Skubi, K. L.; Blum, T. R.; Yoon, T. P. Chem. Rev. 2016, 116, 10035.
(h) Parasram, M.; Gevorgyan, V. Chem. Soc. Rev. 2017, 46, 6227.
(i) Larsen, C. B.; Wenger, O. S. Chem.-Eur. J. 2018, 24, 2039.
(j) Marzo, L.; Pagire, S. K.; Reiser, O.; Konig, B. Angew. Chem., Int. Ed. 2018, 57, 10034.
(k) Zhao, Y. T.; Xia, W. J. Chem. Soc. Rev. 2018, 47, 2591.
(l) Chuentragool, P.; Kurandina, D.; Gevorgyan, V. Angew. Chem., Int. Ed. 2019, 58, 11586.
(m) Zhou, Q. Q.; Zou, Y. Q.; Lu, L. Q.; Xiao, W. J. Angew. Chem., Int. Ed. 2019, 58, 1586.
(n) Xiao, L.; Li, J. H.; Wang, T. Acta Chim. Sinica 2019, 77, 841(in Chinese). (肖丽, 李嘉恒, 王挺, 化学学报, 2019, 77, 841.)
(o) Chen, Y. L.; Chang, L.; Zuo, Z. W. Acta Chim. Sinica 2019, 77, 794(in Chinese). (陈奕霖, 常亮, 左智伟, 化学学报, 2019, 77, 794.)
(p) Chen, D.; Liu, J. C.; Zhang, X. Y.; Jiang, H. Z.; Li, J. H. Chin. J. Org. Chem. 2019, 39, 3353(in Chinese). (陈丹, 刘剑沉, 张馨元, 蒋合众, 李加洪, 有机化学, 2019, 39, 3353.)
(q) Zhang, H.; Yu, S. Y. Chin. J. Org. Chem. 2019, 39, 95(in Chinese). (张昊, 俞寿云, 有机化学, 2019, 39, 95.)
[2] For recent reviews on asymmetric photoredox catalysis, see:(a) Meggers, E. Chem. Commun. 2015, 51, 3290.
(b) Wang, C. F.; Lu, Z. Org. Chem. Front. 2015, 2, 179.
(c) Yoon, T. P. Acc. Chem. Res. 2016, 49, 2307.
(d) Wang, D. H.; Zhang, L.; Luo, S. Z. Acta Chim. Sinica 2017, 75, 22(in Chinese). (王德红, 张龙, 罗三中, 化学学报, 2017, 75, 22.)
(e) Brenninger, C.; Jolliffe, J. D.; Bach, T. Angew. Chem., Int. Ed. 2018, 57, 14338.
(f) Garrido-Castro, A. F.; Maestro, M. C.; Aleman, J. Tetrahedron Lett. 2018, 59, 1286.
(g) Silvi, M.; Melchiorre, P. Nature 2018, 554, 41.
(h) Zou, Y. Q.; Hormann, F. M.; Bach, T. Chem. Soc. Rev. 2018, 47, 278.
(i) Jiang, C.; Chen, W.; Zheng, W. H.; Lu, H. Org. Biomol. Chem. 2019, 17, 867
[3] For examples of deracemization enabled by visible-light photocatalysis, see:(a) Hoelzl-Hobmeier, A.; Bauer, A.; Silva, A. V.; Huber, S. M.; Bannwarth, C.; Bach, T. Nature 2018, 564, 240.
(b) Shin, N. Y.; Ryss, J. M.; Zhang, X.; Miller, S. J.; Knowles, R. R. Science 2019, 366, 364.
(c) Troster, A.; Bauer, A.; Jandl, C.; Bach, T. Angew. Chem., Int. Ed. 2019, 58, 3538.
(d) Shi, Q.; Ye, J. Angew. Chem., Int. Ed. 2020, 59, 4998.
[4] For selected examples of dual catalysis systems, see:(a) Blum, T. R.; Miller, Z. D.; Bates, D. M.; Guzei, I. A.; Yoon, T. P. Science 2016, 354, 1391.
(b) Capacci, A. G.; Malinowski, J. T.; McAlpine, N. J.; Kuhne, J.; MacMillan, D. W. C. Nat. Chem. 2017, 9, 1073.
(c) Lin, L.; Bai, X.; Ye, X.; Zhao, X.; Tan, C. H.; Jiang, Z. Angew. Chem., Int. Ed. 2017, 56, 13842.
(d) Yang, Q.; Zhang, L.; Ye, C.; Luo, S. Z.; Wu, L. Z.; Tung, C. H. Angew. Chem., Int. Ed. 2017, 56, 3694.
(e) Proctor, R. S. J.; Davis, H. J.; Phipps, R. J. Science 2018, 360, 419.
(f) Ye, C.-X.; Melcamu, Y. Y.; Li, H.-H.; Cheng, J.-T.; Zhang, T.-T.; Ruan, Y.-P.; Zheng, X.; Lu, X.; Huang, P.-Q. Nat. Commun. 2018, 9, 410.
(g) Zhang, H. H.; Zhao, J. J.; Yu, S. J. Am. Chem. Soc. 2018, 140, 16914.
(h) Cheng, Y. Z.; Zhao, Q. R.; Zhang, X.; You, S. L. Angew. Chem., Int. Ed. 2019, 58, 18069.
(i) Li, Y.; Lei, M.; Gong, L. Nat. Catal. 2019, 2, 1016.
(j) Zhang, K.; Lu, L. Q.; Jia, Y.; Wang, Y.; Lu, F. D.; Pan, F.; Xiao, W. J. Angew. Chem., Int. Ed. 2019, 58, 13375.
(k) Cheng, Z. M.; Chen, P. H.; Liu, G. S. Acta Chim. Sinica 2019, 77, 856(in Chinese). (成忠明, 陈品红, 刘国生, 化学学报, 2019, 77, 856.)
[5] For selected examples of bifunctional photocatalysts, see:(a) Arceo, E.; Jurberg, I. D.; Alvarez-Fernandez, A.; Melchiorre, P. Nat. Chem. 2013, 5, 750.
(b) Ding, W.; Lu, L. Q.; Zhou, Q. Q.; Wei, Y.; Chen, J. R.; Xiao, W. J. J. Am. Chem. Soc. 2017, 139, 63.
(c) Silvi, M.; Verrier, C.; Rey, Y. P.; Buzzetti, L.; Melchiorre, P. Nat. Chem. 2017, 9, 868.
(d) Skubi, K. L.; Kidd, J. B.; Jung, H.; Guzei, I. A.; Baik, M. H.; Yoon, T. P. J. Am. Chem. Soc. 2017, 139, 17186.
(e) Li, Y.; Zhou, K.; Wen, Z.; Cao, S.; Shen, X.; Lei, M.; Gong, L. J. Am. Chem. Soc. 2018, 140, 15850.
(f) Rigotti, T.; Casado-Sanchez, A.; Cabrera, S.; Perez-Ruiz, R.; Liras, M.; O'Shea, V. A. D.; Aleman, J. ACS Catal. 2018, 8, 5928.
(g) Shen, X.; Li, Y.; Wen, Z.; Cao, S.; Hou, X.; Gong, L. Chem. Sci. 2018, 9, 4562.
(h) Stegbauer, S.; Jandl, C.; Bach, T. Angew. Chem., Int. Ed. 2018, 57, 14593.
(i) Guo, Q.; Wang, M.; Peng, Q.; Huo, Y.; Liu, Q.; Wang, R.; Xu, Z. ACS Catal. 2019, 9, 4470.
[6] (a) Giese, B. Angew. Chem., Int. Ed. 1983, 22, 753.
(b) Giese, B.; González-Gómez, J. A.; Witzel, T. Angew. Chem., Int. Ed. 1984, 23, 69.
[7] (a) Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029.
(b) Sibi, M. P.; Ji, J.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200.
(c) Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163.
[8] Espelt, L. R.; McPherson, I. S.; Wiensch, E. M.; Yoon, T. P. J. Am. Chem. Soc. 2015, 137, 2452.
[9] (a) Zuo, Z. W.; Ahneman, D. T.; Chu, L. L.; Terrett, J. A.; Doyle, A. G.; MacMillan, D. W. C. Science 2014, 345, 437.
(b) Zuo, Z. W.; Gong, H.; Li, W.; Choi, J.; Fu, G. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2016, 138, 1832.
[10] For accounts on synthetic utilization of α-aminoalkyl radicals in visible-light photoredox catalysis, see:(a) Cho, D. W.; Yoon, U. C.; Mariano, P. S. Acc. Chem. Res. 2011, 44, 204.
(b) Nakajima, K.; Miyake, Y.; Nishibayashi, Y. Acc. Chem. Res. 2016, 49, 1946.
[11] (a) Cermenati, L.; Mella, M.; Albini, A. Tetrahedron 1998, 54, 2575.
(b) Smitha, M. A.; Prasad, E.; Gopidas, K. R. J. Am. Chem. Soc. 2001, 123, 1159.
(c) Yoshimi, Y.; Kobayashi, K.; Kamakura, H.; Nishikawa, K.; Haga, Y.; Maeda, K.; Morita, T.; Itou, T.; Okada, Y.; Hatanaka, M. Tetrahedron Lett. 2010, 51, 2332.
(d) Miyake, Y.; Nakajima, K.; Nishibayashi, Y. Chem. Commun. 2013, 49, 7854.
(e) Lang, S. B.; O'Nele, K. M.; Tunge, J. A. J. Am. Chem. Soc. 2014, 136, 13606.
[12] (a) Bauer, E. B. Chem. Soc. Rev. 2012, 41, 3153.
(b) Cao, Z.-Y.; Brittain, W. D. G.; Fossey, J. S.; Zhou, F. Catal. Sci. Technol. 2015, 5, 3441.
(c) Zhang, L.; Meggers, E. Chem.-Asian. J. 2017, 12, 2335.
(d) Cruchter, T.; Larionov, V. A. Coord. Chem. Rev. 2018, 376, 95.
[13] Lin, S. X.; Sun, G. J.; Kang, Q. Chem. Commun. 2017, 53, 7665.
[14] CCDC 1998446 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
[15] (a) Ohta, S.; Hayakawa, S.; Nishimura, K.; Okamoto, M. Chem. Pharm. Bull. 1987, 35, 1058.
(b) Miyashita, A.; Suzuki, Y.; Nagasaki, I.; Ishiguro, C.; Iwamoto, K.-I.; Higashino, T. Chem. Pharm. Bull. 1997, 45, 1254.
[16] (a) de Assis, F. F.; Huang, X.; Akiyama, M.; Pilli, R. A.; Meggers, E. J. Org. Chem. 2018, 83, 10922.
(b) Ma, J.; Lin, J.; Zhao, L.; Harms, K.; Marsch, M.; Xie, X.; Meggers, E. Angew. Chem., Int. Ed. 2018, 57, 11193.
[17] Wang, C.; Chen, L. A.; Huo, H.; Shen, X.; Harms, K.; Gong, L.; Meggers, E. Chem. Sci. 2015, 6, 1094.
[18] Huo, H.; Shen, X.; Wang, C.; Zhang, L.; Rose, P.; Chen, L. A.; Harms, K.; Marsch, M.; Hilt, G.; Meggers, E. Nature 2014, 515, 100.

中心手性金属铑配合物催化的不对称光诱导Giese自由基加成反应

Asymmetric Photoinduced Giese Radical Addition Enabled by a Single Chiral-at-Metal Rhodium Complex

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 15

编辑推荐

相关统计

本文评价

[1]	童红恩, 郭宏宇, 周荣. 可见光促进惰性碳-氢键对羰基的加成反应进展[J]. 有机化学, 2024, 44(1): 54-69.
[2]	朱彦硕, 王红言, 舒朋华, 张克娜, 王琪琳. 烷氧自由基引发1,5-氢原子转移实现C(sp³)—H键官能团化的研究进展[J]. 有机化学, 2024, 44(1): 1-17.
[3]	杨晓娜, 郭宏宇, 周荣. 可见光促进有机硅化合物参与的化学转化[J]. 有机化学, 2023, 43(8): 2720-2742.
[4]	高艳华, 张银潘, 张妍, 宋涛, 杨勇. 可见光驱动表面富含氧空位Nb₂O₅催化醇氧化反应[J]. 有机化学, 2023, 43(7): 2572-2579.
[5]	赵金晓, 魏彤辉, 柯森, 李毅. 可见光催化合成二氟烷基取代的多环吲哚化合物[J]. 有机化学, 2023, 43(3): 1102-1114.
[6]	赵瑜, 段玉荣, 史时辉, 白育斌, 黄亮珠, 杨晓军, 张琰图, 冯彬, 张建波, 张秋禹. 可见光促进高价碘(III)试剂参与反应的研究进展[J]. 有机化学, 2023, 43(12): 4106-4140.
[7]	陈凤娟, 刘罗, 张子露, 曾伟. 可见光催化有机硅的合成研究进展[J]. 有机化学, 2023, 43(10): 3454-3469.
[8]	朱佳洁, 万义, 袁启洋, 魏金莲, 张永强. 可见光/路易斯碱协同催化的三氟甲基取代烯烃脱氟硅化反应研究[J]. 有机化学, 2023, 43(10): 3623-3634.
[9]	潘振涛, 刘彤, 马永敏, 颜剑波, 王亚军. 布朗斯特酸/可见光氧化还原接力催化构建喹唑啉(硫)酮[J]. 有机化学, 2022, 42(9): 2823-2831.
[10]	李亚东, 吴鹏举, 杨志勇. 可见光催化苯并噁唑与α-酮酸合成芳基苯并噁唑[J]. 有机化学, 2022, 42(6): 1770-1777.
[11]	孙天义, 张依凡, 孟远倢, 王怡, 朱琦峰, 姜玉新, 刘石惠. 可见光-铜共催化的糖类区域选择性氧烷基化反应[J]. 有机化学, 2022, 42(5): 1414-1422.
[12]	杨惜晖, 高皓炜, 闫甲乐, 史雷. 自由基介导的硅烷Si—H键官能团化研究进展: 一种合成含C—Si键有机硅化合物的有效策略[J]. 有机化学, 2022, 42(12): 4122-4151.
[13]	何燕, 黄天姿, 史小琴, 陈艳, 吴琼. 异腈参与的光催化反应研究进展[J]. 有机化学, 2022, 42(12): 4220-4246.
[14]	赵成军, 白治琴, 何建, 刘强. 吡唑化提高喹喔啉酮敏化效率: 氮杂环丁烷的合成及进一步开环反应[J]. 有机化学, 2022, 42(12): 4300-4314.
[15]	季晓霜, 付荣, 王树良, 郝文娟, 姜波. 可见光驱动酚/芳胺联-1,6-烯炔与全卤代甲烷的Kharasch反应[J]. 有机化学, 2022, 42(12): 4282-4291.