光促进十聚钨酸盐催化的C—H键官能团化反应

doi:10.6023/cjoc202006068

摘要/Abstract

近年来，十聚钨酸盐作为催化剂在光催化有机合成领域引起了广泛关注.在光照下，十聚钨酸盐可以活化反应物中的C—H键，通过“氢原子转移”作用产生自由基，进而实现C—H键官能团化反应.对近年来十聚钨酸盐在光诱导下催化C—H键官能团化，构筑C—C、C—N、C—F键等的研究进展进行了综述.

关键词: 十聚钨酸盐, 氢原子转移, 光催化, 自由基, C—H键官能团化

In recent years, decatungstate [W₁₀O₃₂]^4- as a catalyst has attracted much attention in the field of photocatalytic organic synthesis. With the catalysis of decatungstate, the C—H bond of substrate can be converted into the corresponding radical via a hydrogen atom transfer (HAT) progress under light irradiation. In this review, we summarized the recent advances of the application of decatungstate as a photocatalyst for the C—H functionalization to construct C—C, C—N, C—F bonds.

Key words: decatungstate, hydrogen atom transfer (HAT), photocatalysis, radical, C-H functionalization

引用此文

袁晓亚, 杨国平, 於兵. 光促进十聚钨酸盐催化的C—H键官能团化反应[J]. 有机化学, 2020, 40(11): 3620-3632.

Yuan Xiaoya, Yang Guoping, Yu Bing. Photoinduced Decatungstate-Catalyzed C-H Functionalization[J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3620-3632.

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参考文献

[1] (a) Su, F.; Guo, Y. Green Chem. 2014, 16, 2934.
(b) Omwoma, S.; Gore, C. T.; Ji, Y.; Hu, C.; Song, Y.-F. Coord. Chem. Rev. 2015, 286, 17.
(c) Yu, B.; Zou, B.; Hu, C.-W. J. CO₂ Util. 2018, 26, 314.
(d) Wang, S.-S.; Yang, G.-Y. Chem. Rev. 2015, 115, 4893.
(e) Yang, G.-P.; Wu, X.; Yu, B.; Hu, C.-W. ACS Sustainable Chem. Eng. 2019, 7, 3727.
(f) Yang, G.-P.; Zhang, N.; Ma, N.-N.; Yu, B.; Hu, C.-W. Adv. Synth. Catal. 2017, 359, 926.
(g) Ma, P.; Hu, F.; Wang, J.; Niu, J. Coord. Chem. Rev. 2019, 378, 281.
(h) Du, D.-Y.; Qin, J.-S.; Li, S.-L.; Su, Z.-M.; Lan, Y.-Q. Chem. Soc. Rev. 2014, 43, 4615.
(i) Chen, L.; Chen, W.-L.; Wang, X.-L.; Li, Y.-G.; Su, Z.-M.; Wang, E.-B. Chem. Soc. Rev. 2019, 48, 260.
(j) Zhang, J.; Huang, Y.; Li, G.; Wei, Y. Coord. Chem. Rev. 2019, 378, 395.
(k) Zhou, Y.; Guo, Z.; Hou, W.; Wang, Q.; Wang, J. Catal. Sci. Technol. 2015, 5, 4324.
(l) Huang, B.; Yang, D.-H.; Han, B.-H. J. Mater. Chem. A 2020, 8, 4593.
[2] Yamase, T.; Sasaki, R.; Ikawa, T. J. Chem. Soc., Dalton Trans. 1981, 628.
[3] Papaconstantinou, E.; Dimotikali, D.; Politou, A. Inorg. Chim. Acta 1980, 43, 155.
[4] Hill, C. L.; Bouchard, D. A. J. Am. Chem. Soc. 1985, 107, 5148.
[5] (a) Wang, M.-Y.; Ma, R.; He, L.-N. Sci. China Chem. 2016, 59, 507.
(b) Lin, J.; Han, Q.; Ding, Y. Chem. Rec. 2018, 18, 1531.
[6] Duncan, D. C.; Netzel, T. L.; Hill, C. L. Inorg. Chem. 1995, 34, 4640.
[7] Waele, V. D.; Poizat, O.; Fagnoni, M.; Bagno, A.; Ravelli, D. ACS Catal. 2016, 6, 7174.
[8] (a) Hartwig, J. F.; Larsen, M. A. ACS Central Sci. 2016, 2, 281.
(b) Fabry, D. C.; Zoller, J.; Rueping, M. Org. Chem. Front. 2019, 6, 2635.
[9] (a) Lü, Q.; Yu, B. J. Liaocheng Univ. (Nat. Sci. Ed.) 2019, 32, 28(in Chinese). (吕琪妍, 於兵, 聊城大学学报(自然科学版), 2019, 32, 28.)
(b) Jiang, Y.-Q.; Li, J.; Feng, Z.-W.; Xu, G.-Q.; Shi, X.; Ding, Q.-J.; Li, W.; Ma, C.-H.; Yu, B. Adv. Synth. Catal. 2020, 362, 2609.
(c) Mao, P.; Zhu, J.; Yuan, J.; Yang, L.; Xiao, Y.; Zhang, C. Chin. J. Org. Chem. 2019, 39, 1529.
(d) Gao, F.; Lü, Q.; Yu, B. J. Liaocheng Univ. (Nat. Sci. Ed.) 2020, 33, 66(in Chinese). (高凡, 吕琪妍, 於兵, 聊城大学学报(自然科学版), 2020, 33, 66.)
[10] (a) Ravelli, D.; Fagnoni, M.; Fukuyama, T.; Nishikawa, T.; Ryu, I. ACS Catal. 2018, 8, 701.
(b) Ravelli, D.; Protti, S.; Fagnoni, M. Acc. Chem. Res. 2016, 49, 2232.
(c) Tzirakis, M. D.; Lykakis, I. N.; Orfanopoulos, M. Chem. Soc. Rev. 2009, 38, 2609.
(d) Suzuki, K.; Mizuno, N.; Yamaguchi, K. ACS Catal. 2018, 8, 10809.
(e) Capaldo, L.; Ravelli, D. Eur. J. Org. Chem. 2017, 2017, 2056.
[11] (a) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1993, 115, 12212.
(b) Hill, C. L. Synlett 1995, 127.
(c) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704.
[12] Zheng, Z.; L. Hill, C. Chem. Commun. 1998, 2467.
[13] (a) Dondi, D.; Fagnoni, M.; Albini, A. Chem. Eur. J. 2006, 12, 4153.
(b) Dondi, D.; Fagnoni, M.; Molinari, A.; Maldotti, A.; Albini, A. Chem. Eur. J. 2004, 10, 142.
(c) Protti, S.; Ravelli, D.; Fagnoni, M.; Albini, A. Chem. Commun. 2009, 7351.
[14] Ravelli, D.; Albini, A.; Fagnoni, M. Chem. Eur. J. 2011, 17, 572.
[15] Ryu, I.; Tani, A.; Fukuyama, T.; Ravelli, D.; Fagnoni, M.; Albini, A. Angew. Chem. Int. Ed. 2011, 50, 1869.
[16] Ravelli, D.; Zoccolillo, M.; Mella, M.; Fagnoni, M. Adv. Synth. Catal. 2014, 356, 2781.
[17] Laudadio, G.; Deng, Y.; van der Wal, K.; Ravelli, D.; Nuño, M.; Fagnoni, M.; Guthrie, D.; Sun, Y.; Noël, T. Science 2020, 369, 92.
[18] Supranovich, V. I.; Levin, V. V.; Dilman, A. D. Org. Lett. 2019, 21, 4271.
[19] Esposti, S.; Dondi, D.; Fagnoni, M.; Albini, A. Angew. Chem., Int. Ed. 2007, 46, 2531.
[20] (a) Kuang, Y.; Wang, K.; Shi, X.; Huang, X.; Meggers, E.; Wu, J. Angew. Chem., Int. Ed. 2019, 58, 16859.
(b) Li, F.; Tian, D.; Fan, Y.; Lee, R.; Lu, G.; Yin, Y.; Qiao, B.; Zhao, X.; Xiao, Z.; Jiang, Z. Nat. Commun. 2019, 10, 1774.
[21] Murphy, J. J.; Bastida, D.; Paria, S.; Fagnoni, M.; Melchiorre, P. Nature 2016, 532, 218.
[22] Dai, Z.-Y.; Nong, Z.-S.; Wang, P.-S. ACS Catal. 2020, 10, 4786.
[23] Quattrini, M. C.; Fujii, S.; Yamada, K.; Fukuyama, T.; Ravelli, D.; Fagnoni, M.; Ryu, I. Chem. Commun. 2017, 53, 2335.
[24] Perry, I. B.; Brewer, T. F.; Sarver, P. J.; Schultz, D. M.; DiRocco, D. A.; MacMillan, D. W. C. Nature 2018, 560, 70.
[25] (a) Kong, Y.; Xu, X.; Ye, F.; Weng, J. Chin. J. Org. Chem. 2019, 39, 3065(in Chinese). (孔瑶蕾; 徐雯秀; 叶飞霞; 翁建全, 有机化学, 2019, 39, 3065.)
(b) Xiong, L.; Hu, H.; Wei, C.-W.; Yu, B. Eur. J. Org. Chem. 2020, 1588.
[26] (a) Chen, F.; Chen, H.; Wu, Q.; Luo, S. Chin. J. Org. Chem. 2020, 40, 339(in Chinese). (陈锋, 陈浩, 吴庆安, 罗书平, 有机化学, 2020, 40, 339.)
(b) Wang, H.; Gao, X.; Lv, Z.; Abdelilah, T.; Lei, A. Chem. Rev. 2019, 119, 6769.
(c) Zhong, J.; Meng, Q.; Tong, Z.; Wu, L. Acta Chem. Sinica 2017, 75, 34(in Chinese). (钟建基; 孟庆元; 陈彬; 佟振合; 吴骊珠, 化学学报, 2017, 75, 34.)
(d) Chen, B.; Wu, L.-Z.; Tung, C.-H. Acc. Chem. Res. 2018, 51, 2512.
[27] Cao, H.; Kuang, Y.; Shi, X.; Wong, K. L.; Tan, B. B.; Kwan, J. M. C.; Liu, X.; Wu, J. Nat. Commun. 2020, 11, 1956.
[28] Yahata, K.; Sakurai, S.; Hori, S.; Yoshioka, S.; Kaneko, Y.; Hasegawa, K.; Akai, S. Org. Lett. 2020, 22, 1199.
[29] (a) Ji, X.; Shi, G.; Zhang, Y. Chin. J. Org. Chem. 2019, 39, 929(in Chinese). (季小明, 史广法, 张扬会, 有机化学, 2019, 39, 929.)
(b) Liu, T.; Qu, C.; Xie, J.; Zhu, C. Chin. J. Org. Chem. 2019, 39, 1613(in Chinese). (刘涛, 屈川华, 谢劲, 朱成建, 有机化学, 2019, 39, 1613.)
(c) Zeng, F.-L.; Sun, K.; Chen, X.-L.; Yuan, X.-Y.; He, S.-Q.; Liu, Y.; Peng, Y.-Y.; Qu, L.-B.; Lv, Q.-Y.; Yu, B. Adv. Synth. Catal. 2019, 361, 5176.
(d) Wang, J.; Sun, K.; Chen, X.; Chen, T.; Liu, Y.; Qu, L.; Zhao, Y.; Yu, B. Org. Lett. 2019, 21, 1863.
[30] Sarver, P. J.; Bacauanu, V.; Schultz, D. M.; DiRocco, D. A.; Lam, Y.-H.; Sherer, E. C.; MacMillan, D. W. C. Nat. Chem. 2020, 12, 459.
[31] (a) Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991.
(b) Bennasar, M. L.; Roca, T.; Griera, R.; Bosch, J. Org. Lett. 2001, 3, 1697.
(c) Bath, S.; Laso, N. M.; Lopez-Ruiz, H.; Quiclet-Sire, B.; Zard, S. Z. Chem. Commun. 2003, 204.
(d) Benati, L.; Calestani, G.; Leardini, R.; Minozzi, M.; Nanni, D.; Spagnolo, P.; Strazzari, S. Org. Lett. 2003, 5, 1313.
[32] Fan, P.; Zhang, C.; Lan, Y.; Lin, Z.; Zhang, L.; Wang, C. Chem. Commun. 2019, 55, 12691.
[33] Fan, P.; Lan, Y.; Zhang, C.; Wang, C. J. Am. Chem. Soc. 2020, 142, 2180.
[34] Fan, P.; Zhang, C.; Zhang, L.; Wang, C. Org. Lett. 2020, 22, 3875.
[35] Schirmer, T. E.; Wimmer, A.; Weinzierl, F. W. C.; König, B. Chem. Commun. 2019, 55, 10796.
[36] Wang, L.; Wang, T.; Cheng, G.-J.; Li, X.; Wei, J.-J.; Guo, B.; Zheng, C.; Chen, G.; Ran, C.; Zheng, C. ACS Catal. 2020, 10, 7543.
[37] Dong, J.; Wang, X.; Wang, Z.; Song, H.; Liu, Y.; Wang, Q. Chem. Sci. 2020, 11, 1026.
[38] Okada, M.; Fukuyama, T.; Yamada, K.; Ryu, I.; Ravelli, D.; Fagnoni, M. Chem. Sci. 2014, 5, 2893.
[39] Ryu, I.; Tani, A.; Fukuyama, T.; Ravelli, D.; Montanaro, S.; Fagnoni, M. Org. Lett. 2013, 15, 2554.
[40] Halperin, S. D.; Fan, H.; Chang, S.; Martin, R. E.; Britton, R. Angew. Chem., Int. Ed. 2014, 53, 4690.
[41] Halperin, S. D.; Kwon, D.; Holmes, M.; Regalado, E. L.; Campeau, L.-C.; DiRocco, D. A.; Britton, R. Org. Lett. 2015, 17, 5200.