综述与进展

可见光催化偕二氟烯烃碳-氟键官能化反应的研究进展

  • 李志清 ,
  • 邱潇杨 ,
  • 娄江 ,
  • 王强
展开
  • a 齐鲁工业大学(山东省科学院) 生物基材料与绿色造纸国家重点实验室 济南 250353
    b 山东潍坊润丰化工股份有限公司 山东潍坊 261000

收稿日期: 2021-06-06

  修回日期: 2021-07-01

  网络出版日期: 2021-07-20

基金资助

国家自然科学基金(22001140); 山东省自然科学基金(ZR2020QB002); 山东省高等学校优秀青年创新团队支持计划(242007040109)

Progress in Visible-Light Catalyzed C—F Bond Functionalization of gem-Difluoroalkenes

  • Zhiqing Li ,
  • Xiaoyang Qiu ,
  • Jiang Lou ,
  • Qiang Wang
Expand
  • a State Key Laboratory of Biobased Material and Green Papermaking, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353
    b Shandong Weifang Rainbow Chemical Co. Ltd., Weifang, Shandong 261000
* Corresponding authors. E-mail: ,

Received date: 2021-06-06

  Revised date: 2021-07-01

  Online published: 2021-07-20

Supported by

National Natural Science Foundation of China(22001140); Natural Science Foundation of Shandong Province(ZR2020QB002); Outstanding Youth Innovation Team Project of Shandong Provincial University(242007040109)

摘要

单氟烯烃结构单元广泛存在于药物及天然产物等复杂功能分子中, 同时也是重要的有机合成子, 在医药、生物和材料等领域具有广泛的应用. 因此, 开发绿色、经济且高效的合成单氟烯烃化合物的方法具有重要的科学意义和现实价值. 偕二氟烯烃C—F键官能化是制备单氟烯烃化合物的有效手段, 总结了在可见光氧化还原催化、可见光氧化还原/过渡金属协同催化条件下实现偕二氟烯烃C—F键官能化反应的研究进展, 主要介绍了底物适用范围、反应机理和合成应用, 并对它的发展前景进行了展望.

本文引用格式

李志清 , 邱潇杨 , 娄江 , 王强 . 可见光催化偕二氟烯烃碳-氟键官能化反应的研究进展[J]. 有机化学, 2021 , 41(11) : 4192 -4207 . DOI: 10.6023/cjoc202106013

Abstract

Monofluoroalkene structural units widely exist in complex functional molecules such as drugs and natural products. They are also critical organic synthons with broad applications in medicine, biology, materials and other fields. Therefore, it is of great scientific significance and practical value to develop green, economical and efficient methods for synthesizing monofluoroalkenes. Functionalization of the C—F bond of gem-difluoroalkenes is an effective method to prepare monofluoroalkenes. The research progress in C—F bond functionalization of gem-difluoroalkenes under visible-light redox catalysis and visible-light redox/transition-metal synergistic catalysis, including the substrate scope, reaction mechanism, and synthesis applications, is summarized. Finally, the prospects of this reaction are also discussed.

参考文献

[1]
(a) Johnson, B. M.; Shu, Y.-Z.; Zhuo, X.; Meanwell, N. A. J. Med. Chem. 2020, 63, 6315.
[1]
(b) Mei, H.; Han, J.; Fustero, S.; Medio-Simon, M.; Sedgwick, D. M.; Santi, C.; Ruzziconi, R.; Soloshonok, V. A. Chem.-Eur. J. 2019, 25, 11797.
[1]
(c) Liu, H.; Ge, L.; Wang, D.-X.; Chen, N.; Feng, C. Angew. Chem., Int. Ed. 2019, 58, 3918.
[1]
(d) Rong, J.; Ni, C.; Wang, Y.; Kuang, C.; Gu, Y.; Hu, J. Acta Chim. Sinica 2017, 75, 105. (in Chinese)
[1]
(荣健, 倪传法, 王云泽, 匡翠文, 顾玉诚, 胡金波, 化学学报, 2017, 75, 105.)
[1]
(e) Zhou, Y.; Wang, J.; Gu, Z.; Wang, S.; Zhu, W.; Aceña, J. L.; Soloshonok, V. A.; Izawa, K.; Liu, H. Chem. Rev. 2016, 116, 422.
[1]
(f) Zhang, K.; Xu, X.-H.; Qing, F.-L. Chin. J. Org. Chem. 2015, 35, 556. (in Chinese)
[1]
(张柯, 徐修华, 卿凤翎, 有机化学, 2015, 35, 556.)
[1]
(g) Xiao, Y.; Pan, Q.; Zhang, X. Acta Chim. Sinica 2015, 73, 387. (in Chinese)
[1]
(肖玉兰, 潘强, 张新刚, 化学学报, 2015, 73, 387.)
[1]
(h) Gillis, E. P.; Eastman, K. J.; Hill, M. D.; Donnelly, D. J.; Meanwell, N. A. J. Med. Chem. 2015, 58, 8315.
[2]
(a) O'Hagan, D.; Deng, H. Chem. Rev. 2015, 115, 634.
[2]
(b) Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214.
[2]
(c) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
[2]
(d) Thayer, A. M. Chem. Eng. News 2006, 84, 15.
[3]
(a) Sun, H.; Liu, T.; Yu, J.; Lau, T. K.; Zhang, G.; Zhang, Y.; Su, M.; Tang, Y.; Ma, R.; Liu, B.; Liang, J.; Feng, K.; Lu, X.; Guo, X.; Gao, F.; Yan, H. Energy Environ. Sci. 2019, 12, 3328.
[3]
(b) Li, X.; Pan, F.; Sun, C.; Zhang, M.; Wang, Z.; Du, J.; Wang, J.; Xiao, M.; Xue, L.; Zhang, Z.-G.; Zhang, C; Liu, F.; Li, Y. Nat. Commun. 2019, 10, 519.
[3]
(c) Ge, J.; Fan, L.; Wang, J.; Zhang, Q.; Liu, Z.; Zhang, E.; Liu, Q.; Yu, X.; Lu, B. Adv. Energy Mater. 2018, 8, 1801477.
[3]
(d) Ni, C.; Hu, J. Chem. Soc. Rev. 2016, 45, 5441.
[3]
(e) Harsanyi, A.; Sandford, G. Org. Process Res. Dev. 2014, 18, 981.
[3]
(f) Pagliaro, M.; Ciriminna, R. J. Mater. Chem. 2005, 15, 4981.
[3]
(g) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
[4]
(a) Koley, S.; Altman, R. A. Isr. J. Chem. 2020, 60, 313.
[4]
(b) Drouin, M.; Hamel, J.-D.; Paquin, J.-F. Synthesis 2018, 50, 881.
[4]
(c) Zhang, X.; Cao, S. Tetrahedron Lett. 2017, 58, 375.
[4]
(d) Liao, F.; Yu, J.; Zhou, J. Chin. J. Org. Chem. 2017, 37, 2175. (in Chinese)
[4]
(廖富民, 余金生, 周剑, 有机化学, 2017, 37, 2175.)
[4]
(e) Landelle, G.; Bergeron, M.; Turcotte-Savard, M.; Paquin, J. Chem. Soc. Rev. 2011, 40, 2867.
[4]
(f) Yanai, H.; Taguchi, T. Eur. J. Org. Chem. 2011, 5939.
[5]
(a) Sommer, H.; Fürstner, A. Chem.-Eur. J. 2017, 23, 558.
[5]
(b) Zhao, Y.; Jiang, F.; Hu, J. J. Am. Chem. Soc. 2015, 137, 5199.
[5]
(c) Malo-Forest, M.; Landelle, G.; Roy, J.-A.; Lacroix, J.; Gaudreault, R.-C.; Paquin, J.-F. Bioorg. Med. Chem. Lett. 2013, 23, 1712.
[5]
(d) Osada, S.; Sano, S.; Ueyama, M.; Chuman, Y.; Kodama, H.; Sakaguchi, K. Bioorg. Med. Chem. 2010, 18, 605.
[5]
(e) Oishi, S.; Kamitani, H.; Kodera, Y.; Watanabe, K.; Kobayashi, K.; Narumi, T.; Tomita, K.; Ohno, H.; Naito, T.; Kodama, E.; Matsuoka, M.; Fujii, N. Org. Biomol. Chem. 2009, 7, 2872.
[6]
(a) Drouin, M.; Wadhwani, P.; Grage, S. L.; Burck, J.; Reichert, J.; Tremblay, S.; Mayer, M. S.; Diel, C.; Staub, A.; Paquin, J.-F.; Ulrich, A. S. Chem.-Eur. J. 2020, 26, 1511.
[6]
(b) Drouin, M.; Arenas, J. L.; Paquin, J. F. ChemBioChem 2019, 20, 1817.
[6]
(c) Drouin, M.; Paquin, J.-F. Beilstein J. Org. Chem. 2017, 13, 2637.
[6]
(d) Zhao, Y.; Jiang, F.; Hu, J. J. Am. Chem. Soc. 2015, 137, 5199.
[7]
Macias, F. A.; De Siqueira, J. M.; Chinchilla, N.; Marin, D.; Varela, R. M.; Molinillo, J. M. G. J. Agric. Food Chem. 2006, 54, 9843.
[8]
(a) Babudri, F.; Cardone, A.; Farinola, G. M.; Martinelli, C.; Mendichi, R.; Naso, F.; Striccoli, M. Eur. J. Org. Chem. 2008, 1977.
[8]
(b) Babudri, F.; Farinola, G. M.; Naso, F.; Ragni, R. Chem. Commun. 2007, 1003.
[9]
(a) Guérin, D.; Gaumont, A.-C.; Dez, I.; Mauduit, M.; Couve- Bonnaire, S.; Pannecoucke, X. ACS Catal. 2014, 4, 2374.
[9]
(b) Dai, W.; Xiao, J.; Jin, G.; Wu, J.; Cao, S. J. Org. Chem. 2014, 79, 10537.
[9]
(c) Debien, L.; Quiclet-Sire, B.; Zard, S. S. Org. Lett. 2012, 14, 5118.
[9]
(d) Wong, O. A.; Shi, Y. J. Org. Chem. 2009, 74, 8377.
[9]
(e) Dutheuil, G.; Couve-Bonnaire, S.; Pannecoucke, X. Angew. Chem., Int. Ed. 2007, 46, 1290.
[10]
(a) Drouin, M.; Hamel, J.-D.; Paquin, J.-F. Synlett 2016, 27, 821.
[10]
(b) Champagne, P. A.; Desroches, J.; Hamel, J.-D.; Vandamme, M.; Paquin, J.-F. Chem. Rev. 2015, 115, 9073.
[10]
(c) Couve-Bonnaire, S.; Cahard, D.; Pannecoucke, X. Org. Biomol. Chem. 2007, 5, 1151.
[11]
(a) Zhang, H.; Wang, E.; Geng, S.; Liu, Z.; He, Y.; Peng, Q.; Feng, Z. Angew. Chem., Int. Ed. 2021, 60, 10211.
[11]
(b) Sakaguchi, H.; Ohashi, M.; Ogoshi, S. Angew. Chem., Int. Ed. 2018, 57, 328.
[11]
(c) Tan, D.-H.; Lin, E.; Ji, W.-W.; Zeng, Y.-F.; Fan, W.-X.; Li, Q.; Gao, H.; Wang, H. Adv. Synth. Catal. 2018, 360, 1032.
[12]
(a) Yan, S.-S.; Wu, D.-S.; Ye, J.-H.; Gong, L.; Zeng, X.; Ran, C.-K.; Gui, Y.-Y.; Li, J.; Yu, D.-G. ACS Catal. 2019, 9, 6987.
[12]
(b) Hu, J.; Zhao, Y.; Shi?, Z. Nat. Catal. 2018, 1, 860.
[12]
(c) Ito, H.; Seo, T.; Kojima, R.; Kubota, K. Chem. Lett. 2018, 47, 1330.
[12]
(d) Sakaguchi, H.; Uetake, Y.; Ohashi, M.; Niwa, T.; Ogoshi, S.; Hosoya, T. J. Am. Chem. Soc. 2017, 139, 12855.
[12]
(e) Zhang, J.; Dai, W.; Liu, Q.; Cao, S. Org. Lett. 2017, 19, 3283.
[12]
(f) Thornbury, R. T.; Toste, F. D. Angew. Chem., Int. Ed. 2016, 55, 11629.
[12]
(g) Xiong, Y.; Huang, T.; Ji, X.; Wu, J.; Cao, S. Org. Biomol. Chem. 2015, 13, 7389.
[12]
(h) Ohashi, M.; Saijo, H.; Shibata, M.; Ogoshi, S. Eur. J. Org. Chem. 2013, 443.
[13]
(a) Dai, W.; Shi, H.; Zhao, X.; Cao, S. Org. Lett. 2016, 18, 4284.
[13]
(b) Dai, W.; Zhang, X.; Zhang, J.; Lin, Y.; Cao, S. Adv. Synth. Catal. 2016, 358, 183.
[13]
(c) Dai, W.; Xiao, J.; Jin, G.; Wu, J.; Cao, S. J. Org. Chem. 2014, 79, 10537.
[13]
(d) Yamada, S.; Shimoji, K.; Takahashi, T.; Konno, T.; Ishihara, T. Chem.-Asian J. 2010, 5, 1846.
[13]
(e) Yamada, S.; Noma, M.; Hondo, K.; Konno, T.; Ishihara, T. J. Org. Chem. 2008, 73, 522.
[13]
(f) Yamada, S.; Noma, M.; Konno, T.; Ishihara, T.; Yamanaka, H. Org. Lett. 2006, 8, 743.
[14]
(a) Zhang, J.; Wang, B.; Liu, S.; Cao, S. Chin. J. Org. Chem. 2019, 39, 249. (in Chinese)
[14]
(张娟, 王碧云, 刘熠森, 曹松, 有机化学, 2019, 39, 249.)
[14]
(b) Ohashi, M.; Kambara, T.; Hatanaka, T.; Saijo, H.; Doi, R.; Ogoshi, S. J. Am. Chem. Soc. 2011, 133, 3256.
[14]
(c) Takachi, M.; Kita, Y.; Tobisu, M.; Fukumoto, Y.; Chatani, N. Angew. Chem., Int. Ed. 2010, 49, 8717.
[14]
(d) Saeki, T.; Takashima, Y.; Tamao, K. Synlett 2005, 1771.
[15]
Wu, F.-P.; Yuan, Y.; Liu, J.; Wu, X.-F. Angew. Chem., Int. Ed. 2021, 60, 8818.
[16]
Ma, Q.; Wang, Y.; Tsui, G. C. Angew. Chem., Int. Ed. 2020, 59, 11293.
[17]
(a) Song, S.; Liu, H.; Wang, L.; Zhu, L.; Loh, T.-P.; Feng, C. Chin. J. Chem. 2019, 37, 1036.
[17]
(b) Zhou, L.; Zhu, C.; Loh, T.-P.; Feng, C. Chem. Commun. 2018, 54, 5618.
[17]
(c) Tian, M.; Yang, X.; Zhang, B.; Liu, B.; Li, X. Org. Chem. Front. 2018, 5, 3406.
[17]
(d) Li, N.; Chang, J.; Kong, L.; Li, X. Org. Chem. Front. 2018, 5, 1978.
[17]
(e) Gong, T.-J.; Xu, M.-Y.; Yu, S.-H.; Yu, C.-G.; Su, W.; Lu, X.; Xiao, B.; Fu, Y. Org. Lett. 2018, 20, 570.
[17]
(f) Murakami, N.; Yoshida, M.; Yoshino, T.; Matsunaga, S. Chem. Pharm. Bull. 2018, 6, 51.
[17]
(g) Wu, J.-Q.; Zhang, S.-S.; Gao, H.; Qi, Z.; Zhou, C.-J.; Ji, W.-W.; Liu, Y.; Chen, Y.; Li, Q.; Li, X.; Wang, H. J. Am. Chem. Soc. 2017, 139, 3537.
[17]
(h) Zell, D.; Dhawa, U.; Müller, V.; Bursch, M.; Grimme, S.; Ackermann, L. ACS Catal. 2017, 7, 4209.
[17]
(i) Cai, S.-H.; Ye, L.; Wang, D.-X.; Wang, Y.-Q.; Lai, L.-J.; Zhu, C.; Feng, C.; Loh, T.-P. Chem. Commun. 2017, 53, 8731.
[17]
(j) Kong, L.; Liu, B.; Zhou, X.; Wang, F.; Li, X. Chem. Commun. 2017, 53, 10326.
[17]
(k) Zell, D.; Meller, V.; Dhawa, U.; Bursch, M.; Presa, R. R.; Grimme, S.; Ackermann, L. Chem.-Eur. J. 2017, 23, 12145.
[17]
(l) Tian, P.; Feng, C.; Loh, T.-P. Nat. Commun. 2015, 6, 7472.
[18]
(a) Amii, H.; Uneyama, K. Chem. Rev. 2009, 109, 2119.
[18]
(b) Ichikawa, J. Chim. Oggi 2007, 25, 54.
[19]
(a) Cannalire, R.; Pelliccia, S.; Sancineto, L.; Novellino, E.; Tron, G. C.; Giustiniano, M. Chem. Soc. Rev. 2021, 50, 766.
[19]
(b) Yu, X.-Y.; Chen, J.-R.; Xiao, W.-J. Chem. Rev. 2021, 121, 506.
[19]
(c) Li, Z.; Jin, J.; Huang, S. Chin. J. Org. Chem. 2020, 40, 563. (in Chinese)
[19]
(李祯龙, 金健, 黄莎华, 有机化学, 2020, 40, 563.)
[19]
(d) Zhou, Q.-Q.; Zou, Y.-Q.; Lu, L.-Q.; Xiao, W.-J. Angew. Chem., Int. Ed. 2019, 58, 1586.
[19]
(e) Kong, Y.; Xu, W.; Ye, F.; Weng, J. Chin. J. Org. Chem. 2019, 39, 3065. (in Chinese)
[19]
(孔瑶蕾, 徐雯秀, 叶飞霞, 翁建全, 有机化学, 2019, 39, 3065.)
[19]
(f) Parasram, M.; Gevorgyan, V. Chem. Soc. Rev. 2017, 46, 6227.
[20]
(a) Leifert, D.; Studer, A. Angew. Chem., Int. Ed. 2020, 59, 74.
[20]
(b) Wang, S.; Tang, S.; Lei, A. Sci. Bull. 2018, 63, 1006.
[20]
(c) Yi, H.; Zhang, G.; Wang, H.; Huang, Z.; Wang, J.; Singh, A. K.; Lei, A. Chem. Rev. 2017, 117, 9016.
[20]
(d) Xie, J.; Jin, H.; Hashmi, A. S. K. Chem. Soc. Rev. 2017, 46, 5193.
[20]
(e) Togo, H. Advanced Free Radical Reactions for Organic Synthesis, Elsevier, Amsterdam, 2004, pp. 1-2.
[21]
(a) Nobile, E.; Castanheiro, T.; Besset, T. Angew. Chem., Int. Ed. 2021, 60, 12170.
[21]
(b) Wu, X.; Zhu, C. Acc. Chem. Res. 2020, 53, 1620.
[22]
Xie, J.; Yu, J.; Rudolph, M.; Rominger, F.; Hashmi, A. S. K. Angew. Chem., Int. Ed. 2016, 55, 9416.
[23]
(a) Wilkinson, B.; Zhu, M.; Priestley, N. D.; Nguyen, H. H. T.; Morimoto, H.; Williams, P. G.; Chan, S. I.; Floss, H. G. J. Am. Chem. Soc. 1996, 118, 921.
[23]
(b) Step, E. N.; Turro, N. J. J. Photochem. Photobiol. A 1994, 84, 249.
[23]
(c) Scaiano, J. C. J. Phys. Chem. 1981, 85, 2851.
[23]
(d) Livant, P.; Lawler, R. G. J. Am. Chem. Soc. 1976, 98, 6044.
[24]
Tian, H.; Xia, Q.; Wang, Q.; Dong, J.; Liu, Y.; Wang, Q. Org. Lett. 2019, 21, 4585.
[25]
(a) Zuo, Z.; Ahneman, D. T.; Chu, L.; Terrett, J. A.; Doyle, A. G.; MacMillan, D. W. C. Science 2014, 345, 437.
[25]
(b) Lowry, M. S.; Goldsmith, J. I.; Slinker, J. D.; Rohl, R.; Pascal, R. A.; Malliaras, G. G.; Bernhard, S. Chem. Mater. 2005, 17, 5712.
[26]
Jeffrey, J. L.; Terrett, J. A.; MacMillan, D. W. C. Science 2015, 349, 1532.
[27]
Xie, J.; Yu, J.; Rudolph, M.; Rominger, F.; Hashmi, A. S. K. Angew. Chem., Int. Ed. 2016, 55, 9416.
[28]
(a) Chen, H.; Liu, Y. A.; Liao, X. Synthesis 2021, 53, 1.
[28]
(b) McMurray, L.; McGuire, T. M.; Howells, R. L. Synthesis 2020, 52, 1719.
[28]
(c) Zhou, M.; Qin, P.; Jing, L.; Sun, J.; Du, H. Chin. J. Org. Chem. 2020, 40, 598. (in Chinese)
[28]
(周明东, 覃丕涛, 经理珂, 孙京, 杜海武, 有机化学, 2020, 40, 598.)
[28]
(d) Liu, J.-Q.; Shatskiy, A.; Matsuura, B. S.; Kärkäs, M. D. Synthesis 2019, 51, 2759.
[28]
(e) Rahman, M.; Mukherjee, A.; Kovalev, I. S.; Kopchuk, D. S.; Zyryanov, G. V.; Tsurkan, M. V.; Majee, A.; Ranu, B. C.; Charushin, V. N.; Chupakhin, O. N.; Santra, S. Adv. Synth. Catal. 2019, 361, 2161.
[28]
(f) Nakajima, K.; Miyake, Y.; Nishibayashi, Y. Acc. Chem. Res. 2016, 49, 1946.
[28]
(g) Xuan, J.; Zhang, Z.-G.; Xiao, W.-J. Angew. Chem., Int. Ed. 2015, 54, 15632.
[29]
Li, J.; Lefebvre, Q.; Yang, H.; Zhao, Y.; Fu, H. Chem. Commun. 2017, 53, 10299.
[30]
Yang, H.; Tian, C.; Qiu, D.; Tian, H.; An, G.; Li, G. Org. Chem. Front. 2019, 6, 2365.
[31]
(a) Xu, W.; Ma, J.; Yuan, X.; Dai, J.; Xie, J.; Zhu, C. Angew. Chem., Int. Ed. 2018, 57, 10357.
[31]
(b) Luo, J.; Zhang, J. ACS Catal. 2016, 6, 873
[32]
Galicia, M.; Gonzalez, F. J. J. Electrochem. Soc. 2002, 149, D46.
[33]
(a) Ye, S.; Wu, J. Acta Chim. Sinica 2019, 77, 814. (in Chinese)
[33]
(叶盛青, 吴劼, 化学学报, 2019, 77, 814.)
[33]
(b) Wang, P.-Z.; Chen, J.-R.; Xiao, W.-J. Org. Biomol. Chem. 2019, 17, 6936.
[33]
(c) Milligan, J. A.; Phelan, J. P.; Badir, S. O.; Molander, G. A. Angew. Chem., Int. Ed. 2019, 58, 6152.
[33]
(d) Huang, W.; Cheng, X. Synlett 2017, 28, 148.
[34]
Du, H.-W.; Sun, J.; Gao, Q.-S.; Wang, J.-Y.; Wang, H.; Xu, Z.; Zhou, M.-D. Org. Lett. 2020, 22, 1542.
[35]
Lemos, A.; Lemaire, C.; Luxen, A. Adv. Synth. Catal. 2019, 361, 1500.
[36]
Wang, P.; Chen, J.; Xiao, W. Org. Biomol. Chem. 2019, 17, 6936.
[37]
(a) Yao, H.; Hu, W.; Zhang, W. Molecules 2021, 26, 105.
[37]
(b) Pang, J.; Wu, J.; Wu, F. Chin. J. Org. Chem. 2021, 41, 983. (in Chinese)
[37]
(潘军, 吴晶晶, 吴范宏, 有机化学, 2021, 41, 983.)
[37]
(c) Wu, Y.-C.; Xiao, Y.-T.; Yang, Y.-Z.; Song, R.-J.; Li, J.-H. ChemCatChem 2020, 12, 5312.
[37]
(d) Wu, X.; Zhu, C. Acc. Chem. Res. 2020, 53, 1620.
[37]
(e) Diccianni, J.; Lin, Q.; Diao, T. Acc. Chem. Res. 2020, 53, 906.
[37]
(f) Jiang, H.; Studer, A. Chem. Soc. Rev. 2020, 49, 1790.
[37]
(g) Li, Z.-L.; Fang, G.-C.; Gu, Q.-S.; Liu, X.-Y. Chem. Soc. Rev. 2020, 49, 32.
[37]
(h) Bao, X.; Li, J.; Jiang, W.; Huo, C. Synthesis 2019, 51, 4507.
[37]
(i) Kawamura, S.; Sodeoka, M. Bull. Chem. Soc. Jpn. 2019, 92, 1245.
[37]
(j) Wang, X.; Studer, A. Acc. Chem. Res. 2017, 50, 1712.
[38]
Wang, Q.; Qu, Y.; Tian, H.; Liu, Y.; Song, H.; Wang, Q. Chem.-Eur. J. 2019, 25, 8686.
[39]
(a) Chen, L.; Francis, H.; Carrow, B. P. ACS Catal. 2018, 8, 2989.
[39]
(b) Bulfield, D.; Huber, S. M. J. Org. Chem. 2017, 82, 13188.
[39]
(c) Chen, L.; Sanchez, D. R.; Zhang, B.; Carrow, B. P. J. Am. Chem. Soc. 2017, 139, 12418.
[39]
(d) Handa, S.; Wang, Y.; Gallou, F.; Lipshutz, B. H. Science 2015, 349, 1087.
[39]
(e) Kinzel, T.; Zhang, Y.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 14073.
[39]
(f) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
[40]
(a) Gao, P.; Yuan, C.; Zhao, Y.; Shi, Z. Chem 2018, 4, 2201.
[40]
(b) Kojima, R.; Akiyama, S.; Ito, H. Angew. Chem., Int. Ed. 2018, 57, 7196.
[40]
(c) Lim, S.; Song, D.; Jeon, S.; Kim, Y.; Kim, H.; Lee, S.; Cho, H.; Lee, B. C.; Kim, S. E.; Kim, K.; Lee, E. Org. Lett. 2018, 20, 7249.
[40]
(d) Sakaguchi, H.; Uetake, Y.; Ohashi, M.; Niwa, T.; Ogoshi, S.; Hsoya, T. J. Am. Chem. Soc. 2017, 139, 12855.
[40]
(e) Liu, Y.; Zhou, Y.; Zhao, Y.; Qu, J. Org. Lett. 2017, 19, 946.
[40]
(f) Zhou, J.; Kuntze-Fechner, M. W.; Bertermann, R.; Paul, U. S. D.; Berthel, J. H. J.; Friedrich, A.; Du, Z.; Marder, T. B.; Radius, U. J. Am. Chem. Soc. 2016, 138, 5250
[40]
(g) Guo, W.-H.; Min, Q.-Q.; Gu, J.-W.; Zhang, X. Angew. Chem., Int. Ed. 2015, 54, 9075.
[41]
Xu, W.; Jiang, H.; Leng, J.; Ong, H.-W.; Wu, J. Angew. Chem., Int. Ed. 2020, 59, 4009.
[42]
(a) Zhu, C.; Yue, H.; Chu, L.; Rueping, M. Chem. Sci. 2020, 11, 4051.
[42]
(b) Abreu, M. D.; Belmont, P.; Brachet, E. Eur. J. Org. Chem. 2020, 2020, 1327.
[42]
(c) Zhang, H.-H.; Yu, S. Acta Chim. Sinica 2019, 77, 832. (in Chinese)
[42]
(张洪浩, 俞寿云, 化学学报, 2019, 77, 832.)
[42]
(d) Wang, C.-S.; Dixneuf, P. H.; Soulé, J.-F. Chem. Rev. 2018, 118, 7532.
[42]
(e) Zhou, W.-J.; Zhang, Y.-H.; Gui, Y.-Y.; Sun, L.; Yu, D.-G. Synthesis 2018, 50, 3359.
[42]
(f) Twilton, J.; Le, C.; Zhang, P.; Shaw, M. H.; Evans, R. W.; MacMillan, D. W. C. Nat. Rev. 2017, 1, 0052.
[42]
(g) Ruan, L.; Dong, Z.; Chen, C.; Wu, S.; Sun, J. Chin. J. Org. Chem. 2017, 37, 2544. (in Chinese)
[42]
(阮利衡, 董振诚, 陈春欣, 吴爽, 孙京, 有机化学, 2017, 37, 2544.)
[42]
(h) Skubi, K. L.; Blum, T. R.; Yoon, T. P. Chem. Rev. 2016, 116, 10035.
[42]
(i) Tellis, J. C.; Kelly, C. B.; Primer, D. N.; Jouffroy, M.; Patel, N. R.; Molander, G. A. Acc. Chem. Res. 2016, 49, 1429.
[43]
Zhu, C.; Zhang, Y.-F.; Liu, Z.-Y.; Zhou, L.; Liu, H.; Feng, C. Chem. Sci. 2019, 10, 6721.
[44]
(a) Li, J.; Luo, Y.; Cheo, H. W.; Lan, Y.; Wu, J. Chem 2019, 5, 192.
[44]
(b) Matsui, J. K.; Gutiérrez-Bonet, Á.; Rotella, M.; Alam, R.; Gutierrez, O.; Molander, G. A. Angew. Chem., Int. Ed. 2018, 57, 15847.
[44]
(c) Meng, Q.-Y.; Wang, S.; Huff, G. S.; König, B. J. Am. Chem. Soc. 2018, 140, 3198.
[44]
(d) Tellis, J. C.; Kelly, C. B.; Primer, D. N.; Jouffroy, M.; Patel, N. R.; Molander, G. A. Acc. Chem. Res. 2016, 49, 1429.
[45]
(a) Chuentragool, P.; Yadagiri, D.; Morita, T.; Sarkar, S.; Parasram, M.; Wang, Y.; Gevorgyan, V. Angew. Chem., Int. Ed. 2019, 58, 1794.
[45]
(b) Ratushnyy, M.; Parasram, M.; Wang, Y.; Gevorgyan, V. Angew. Chem., Int. Ed. 2018, 57, 2712.
[45]
(c) Zhou, W.-J.; Cao, G.-M.; Shen, G.; Zhu, X.-Y.; Gui, Y.-Y.; Ye, J.-H.; Sun, L.; Liao, L.-L.; Li, J.; Yu, D.-G. Angew. Chem., Int. Ed. 2017, 56, 15683.
[45]
(d) Parasram, M.; Gevorgyan, V. Chem. Soc. Rev. 2017, 46, 6227.
[46]
Shimomaki, K.; Murata, K.; Martin, R.; Iwasawa, N. J. Am. Chem. Soc. 2017, 139, 9467.
[47]
Wu, L.-H.; Cheng, J.-K.; Shen, L.; Shen, Z.-L.; Loh, T. P. Adv. Synth. Catal. 2018, 360, 3894.
[48]
Nenajdenko, V. G.; Korotchenko, V. N.; Shastin, A. V.; Balenkova, E. S. Russ. Chem. Bull. 2004, 53, 1034.
[49]
(a) Boyd, D. A. Angew. Chem., Int. Ed. 2016, 55, 15486.
[49]
(b) Feng, M.; Tang, B.; Liang, S.; Jiang, X. Curr. Top. Med. Chem. 2016, 16, 1200.
[49]
(c) Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. J. Med. Chem. 2014, 57, 2832.
[50]
(a) Wang, B.; Zhou, Y.; Luo, S.; Luo, X.; Chen, W.; Yang, S.; Wang, Z. Chin. J. Org. Chem. 2021, 41, 171. (in Chinese)
[50]
(王柏文, 周永军, 罗时荷, 罗晓燕, 陈伟清, 杨诗敏, 汪朝阳, 有机化学, 2021, 41, 171.)
[50]
(b) Lou, J.; Wang, Q.; Wu, P.; Wang, H.; Zhou, Y.-G.; Yu, Z. Chem. Soc. Rev. 2020, 49, 4307.
[50]
(c) Yang, W.; Zhang, M.; Chen, W.; Yang, X.; Feng, J. Chin. J. Org. Chem. 2020, 40, 4060. (in Chinese)
[50]
(杨文超, 张明明, 陈旺, 杨小虎, 冯建国, 有机化学, 2020, 40, 4060.)
[50]
(d) Kaiser, D.; Klose, I.; Oost, R.; Neuhaus, J.; Maulide, N. Chem. Rev. 2019, 119, 8701.
[50]
(e) Wang, L.; He, W.; Yu, Z. Chem. Soc. Rev. 2013, 42, 599.
[51]
Wang, J.; Huang, B.; Yang, C.; Xia, W. Chem. Commun. 2019, 55, 11103.
[52]
Li, Y.; Li, X.; Li, X.; Shi, D. Chem. Commun. 2021, 57, 2152.
文章导航

/