Visible Light-Promoted Isomerization of Alkenes

doi:10.6023/cjoc201809010

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 95-108.DOI: 10.6023/cjoc201809010 Previous Articles Next Articles

Special Issue: 庆祝陈庆云院士九十华诞

Reviews

可见光促进的烯烃异构化反应

张昊^a,b, 俞寿云^b

a 扬州大学化学化工学院扬州 225002;
b 南京大学化学化工学院生命分析化学国家重点实验室南京 210023

收稿日期:2018-09-06 修回日期:2018-10-14 发布日期:2018-10-20
通讯作者: 俞寿云 E-mail:yushouyun@nju.edu.cn
基金资助:
国家自然科学基金（No.21732003）资助项目.

Visible Light-Promoted Isomerization of Alkenes

Zhang Hao^a,b, Yu Shouyun^b

a School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002;
b State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023

Received:2018-09-06 Revised:2018-10-14 Published:2018-10-20
Contact: 10.6023/cjoc201809010 E-mail:yushouyun@nju.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21732003).

The traditional methods for synthesizing Z-olefins generally require the use of high-energy reagents. These methods are usually controlled by kinetics. The reaction conditions are harsh and low atom economic. During the process of separation, Z-olefins are easy to convert to the thermodynamically more stable E-olefins. With the continuous development of organic photochemistry and photocatalysis technology, more and more synthetic challenges have been solved by photocatalysis. Herein, various types of visible light-promoted photocatalytic isomerization of olefins are reviewed.

Key words: photochemistry, olefins, isomerization, energy transfer

Cite this article

Zhang Hao, Yu Shouyun. Visible Light-Promoted Isomerization of Alkenes[J]. Chin. J. Org. Chem., 2019, 39(1): 95-108.

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[1] (a) Pearson, C. M.; Snaddon, T. N. ACS Cent. Sci. 2017, 3, 922.
(b) Cai, W.; Fan, H.; Ding, D.; Zhang, Y.; Wang, W. Chem. Commun. 2017, 53, 12918.
(c) Singh, K.; Staig, S. J.; Weaver, J. D. J. Am. Chem. Soc. 2014, 136, 5275.
(d) Li, X.; Song, S.; Jiao, N. Acta Chim. Sinica 2017, 75, 1202(in Chinese). (李昕伟, 宋颂, 焦宁, 化学学报, 2017, 75, 1202.)
(e) Zhao, M.; Ji, Y. Chin. J. Org. Chem. 2018, 38, 401(in Chinese). (赵明, 纪原, 有机化学, 2018, 38, 401.)
[2] (a) Wittig, G.; Geissler, G. Justus Liebigs Ann. Chem. 1953, 580, 44.
(b) Bergelson, L. D.; Shemyakin, M. M. Tetrahedron 1963, 19, 149.
(c) Dong, D. J.; Li, H.-H.; Tian, S.-K. J. Am. Chem. Soc. 2010, 132, 5018.
[3] (a) Julia, M.; Paris, J.-M. Tetrahedron Lett. 1973, 14, 4833.
(b) Yao, C.-Z.; Li, Q.-Q.; Wang, M.-M.; Ning, X.-S.; Kang, Y.-B. Chem. Commun. 2015, 51, 7729.
[4] (a) Peterson, D. J. J. Org. Chem. 1968, 33, 780.
(b) Staden, L. F. V.; Gravestock, D.; Ager, D. J. Chem. Soc. Rev. 2002, 31, 195.
[5] (a) Koh, M. J.; Khan, R. K. M.; Torker, S.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2014, 53, 1968.
(b) Quigley, B. L.; Grubbs, R. H. Chem. Sci. 2013, 5, 501.
(c) Gottumukkala, A. L.; Madduri, A. V. R.; Minnaard, A. J. ChemCatChem 2012, 4, 462.
(d) Meek, S. J.; O'Brien, R. V.; Llaveria, J.; Schrock, R. R.; Hoveyda, A. H. Nature 2011, 471, 461.
(e) Endo, K.; Grubbs, R. H. J. Am. Chem. Soc. 2011, 133, 8525.
[6] (a) Lindlar, H. Helv. Chim. Acta 1952, 35, 446.
(b) Li, X.; Song, W.; Tang, W. J. Am. Chem. Soc. 2013, 135, 16797.
(c) Song, W.; Li, X.; Yang, K.; Zhao, X.-L.; Glazier, D. A.; Xi, B.-M.; Tang, W. J. Org. Chem. 2016, 81, 2930.
[7] Singh, K.; Staig, S. J.; Weaver, J. D. J. Am. Chem. Soc. 2014, 136, 5275.
[8] Cai, W.; Fan, H.; Ding, D.; Zhang, Y.; Wang, W. Chem. Commun. 2017, 53, 12918.
[9] (a) Wald, G. J. Gen. Physiol. 1935, 19, 351.
(b) O'Leary, B.; Duke, B.; Eilers, J. E. Nature 1973, 246, 166.
(c) Lion, F.; Rotmans, J. P.; Daemen, F. J. M.; Bonting, S. L. Biochim. Biophys. Acta 1975, 384, 283.
(d) Gai, F.; Hasson, K. C.; Cooper McDonald, J.; Anfinrud, P. A. Science 1998, 279, 1886.
(e) Rando, R. R. Chem. Rev. 2001, 101, 1881.
(f) Strauss, O. Physiol. Rev. 2005, 85, 845.
(g) Redmond, T. M.; Poliakov, E.; Yu, S.; Tsai, J.-Y.; Lu, Z.; Gentleman, S. Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 13658.
[10] Metternich, J. B.; Gilmour, R. Synlett 2016, 27, 2541.
[11] (a) Metternich, J. B.; Gilmour, R. J. Am. Chem. Soc. 2015, 137, 11254.
(b) Metternich, J. B.; Artiukhin, D. G.; Holland, M. C.; Bremen-Kühne, M. V.; Neugebauer, J.; Gilmour, R. J. Org. Chem. 2017, 82, 9955.
[12] Walker, A. G.; Radda, G. K. Nature 1967, 215, 1483.
[13] Metternich, J. B.; Gilmour, R. J. Am. Chem. Soc. 2015, 137, 11254.
[14] Metternich, J. B.; Gilmour, R. J. Am. Chem. Soc. 2016, 138, 1040.
[15] Metternich, J. B.; Artiukhin, D. G.; Holland, M. C.; Bremen-Kühne, M. V.; Neugebauer, J.; Gilmour, R. J. Org. Chem. 2017, 82, 9955.
[16] Metternich, J. B.; Sagebiel, S.; Lückener, A.; Lamping, S.; Ravoo, B. J.; Gilmour, R. Chem.-Eur. J. 2018, 24, 4228.
[17] Hammond, G. S.; Saltiel, J.; Lamola, A. A.; Turro, N. J.; Bradshaw, J. S.; Cowan, D. O.; Counsell, R. C.; Vogt, V.; Dalton, C. J. Am. Chem. Soc. 1964, 86, 3197.
[18] (a) Hammond, G. S.; Saltiel, J. J. Am. Chem. Soc. 1962, 84, 4983.
(b) Hammond, G. S.; Saltiel, J. J. Am. Chem. Soc. 1963, 85, 2515.
(c) Hammond, G. S.; Saltiel, J.; Lamola, A. A.; Turro, N. J.; Bradshaw, J. S.; Cowan, D. O.; Counsell, R. C.; Vogt, V.; Dalton, C. J. Am. Chem. Soc. 1964, 86, 3197.
[19] (a) Arai, T.; Sakuragi, H.; Tokumaru, K. Chem. Lett. 1980, 9, 261.
(b) Arai, T.; Sakuragi, H.; Tokumaru, K. Bull. Chem. Soc. Jpn. 1982, 55, 2204.
[20] Zhao, Y.-P.; Yang, L.-Y.; Liu, R. S. H. Green Chem. 2009, 11, 837.
[21] Cai, W.; Fan, H.; Ding, D.; Zhang, Y.; Wang, W. Chem. Commun. 2017, 53, 12918.
[22] Faßbender, S. I.; Metternich, J. B.; Gilmour, R. Org. Lett. 2018, 20, 724.
[23] Osawa, M.; Hoshino, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. 2001, 40, 18.
[24] Rackl, D.; Kreitmeier, P.; Reiser, O. Green Chem. 2016, 18, 214.
[25] Fabry, D. C.; Ronge, M. A.; Rueping, M. Chem. Eur. J. 2015, 21, 5350.
[26] Molloy, J. J.; Metternich, J. B.; Daniliuc, C. G.; Watson, A. J. B.; Gilmour, R. Angew. Chem., Int. Ed. 2018, 57, 3168.
[27] Lin, Q.-Y.; Xu, X.-H.; Qing, F.-L. J. Org. Chem. 2014, 79, 10434.
[28] Iqbal, N.; Jung, J.; Park, S.; Cho, E. J. Angew. Chem., Int. Ed. 2014, 53, 539.
[29] Senaweera, S. M.; Singh, A.; Weaver, J. D. J. Am. Chem. Soc. 2014, 136, 3002.
[30] (a) Singh, A.; Kubik, J. J.; Weaver, J. D. Chem. Sci. 2015, 6, 7206.
(b) Senaweera, S.; Weaver, J. D. J. Am. Chem. Soc. 2016, 138, 2520.
[31] Singh, A.; Fennell, C. J.; Weaver, J. D. Chem. Sci. 2016, 7, 6796.
[32] Zhang, H.; Huang, X. Adv. Synth. Catal. 2016, 358, 3736.
[33] Li, Y.; Miao, T.; Li, P.; Wang, L. Org. Lett. 2018, 20, 1735.
[34] Zheng, C.; Cheng, W.-M.; Li, H.-L.; Na, R.-S.; Shang, R. Org. Lett. 2018, 20, 2559.
[35] Li, J.; Chen, J.; Huang, W.; Cheng, X. Chin. J. Org. Chem. 2018, 38, 1507. (李进, 陈靖之, 黄文浩, 程旭, 有机化学, 2018, 38, 1507.)
[36] An, X.-D.; Zhang, H.; Xu, Q.; Yu, L.; Yu, S. Chin. J. Chem. 2018, 36, 1147.

可见光促进的烯烃异构化反应

Visible Light-Promoted Isomerization of Alkenes

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