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2019 , Vol. 77 >Issue 9: 832 - 840

DOI: https://doi.org/10.6023/A19050177

综述

过渡金属与光氧化还原协同催化的烯丙基取代反应的研究进展

  • 张洪浩 ,
  • 俞寿云
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  • 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
张洪浩, 1991年出生于江苏扬州, 2009年和2013年于江苏师范大学先后获得学士和硕士学位, 2013年至今在俞寿云教授指导下攻读博士学位. 其研究兴趣主要是可见光促进的不对称催化反应.|俞寿云, 1978年11月出生于江苏南京. 2001年获南京大学理学学士学位. 2006年获中国科学院上海有机化学研究所理学博士学位(导师为马大为研究员). 2006年到2007年留所任助理研究员. 2007年-2010年在美国宾夕法尼亚大学进行博士后研究(合作导师Jeffrey W. Bode教授). 2010年9月被聘为南京大学化学化工学院副教授, 博士生导师. 2016年起任南京大学化学化工学院教授. 曾获2012年Thieme Chemistry Journals Award, 2007年国家自然科学二等奖(排名第四)和2005年上海市科技进步一等奖(排名第四)等奖项.

收稿日期: 2019-05-14

  网络出版日期: 2019-07-16

基金资助

项目受国家自然科学基金重点项目资助(No. 21732003)

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Advances on Transition Metals and Photoredox Cooperatively Catalyzed Allylic Substitutions

  • Hong-Hao Zhang, ,
  • Shouyun Yu,
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  • State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering,Nanjing University, Nanjing 210023

Received date: 2019-05-14

  Online published: 2019-07-16

Supported by

Project supported by the National Natural Science Foundation of China(No. 21732003)

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摘要

过渡金属催化的烯丙基取代反应是一类重要且实用的有机化学反应, 可以立体选择性地高效构建碳-碳键和碳-杂键. 可见光氧化还原催化可以利用绿色清洁的可见光能源在较为温和的条件下产生自由基或者自由基离子等高反应活性的反应中间体, 被广泛地应用于有机合成中, 逐渐发展成为一种重要的合成工具. 鉴于烯丙基取代反应的重要性, 过渡金属与光氧化还原协同催化的烯丙基取代反应逐渐引起化学家的兴趣. 该协同催化的策略可以实现单一过渡金属催化难以实现的烯丙基取代反应, 反应的区域选择性和立体选择性也体现出不同的特点, 有望发展成为单一金属催化的烯丙基取代反应的重要补充. 本文综述了近年来不同过渡金属与可见光氧化还原协同催化的烯丙基取代反应的研究进展.

关键词： 烯丙基取代反应; 过渡金属催化; 光氧化还原催化; 协同催化

本文引用格式

张洪浩 , 俞寿云 . 过渡金属与光氧化还原协同催化的烯丙基取代反应的研究进展[J]. 化学学报, 2019 , 77(9) : 832 -840 . DOI: 10.6023/A19050177

Abstract

Allylic substitutions catalyzed by transition metals are important and practical reactions, which can construct carbon-carbon bonds and carbon-heteroatom bonds efficiently and stereoselectively. Various transition metal catalysts, such as Pd, Ir, Cu, Ni, Rh and Ru, have been widely used in this reaction. To date, various “soft”, or stabilized nucleophiles (pKa<25), including malonates, acetoacetates and enolates, have been used in allylic substitutions. Conversely, the high reactivity of “hard”, or non-stabilized alkyl nucleophiles (pKa>25) has limited their utility in catalytic processes and their compatibility with functional groups. Visible light photoredox catalysis has been widely used in organic synthesis because it can generate high reactive intermediates, such as free radicals and radical ions, under mild conditions using green and clean energy, and has gradually developed into an important synthetic tool. Furthermore, merging photoredox catalysis with transition metal catalysts has become a popular strategy for expanding the synthetic utility of visible-light photocatalysis, and has led to the discovery of novel reaction modes. Due to the high activity of the intermediates in photoredox catalysis, the selectivity of these reactions, especially stereoselectivity, is still a challenge. In view of the importance of allyl substitutions, the allyl substitution co-catalyzed by transition metals and photoredox has attracted the interest of chemists. The synergistic strategy can realize allylic substitutions which are difficult to be achieved by single transition metal catalysis. The regioselectivity and stereoselectivity of these reactions also show different characteristics. It is expected to become an important complement to allylic substitution catalyzed by single metal. In this review, recent advances on allylic substitution co-catalyzed by different transition metals and photoredox are summarized. Meanwhile, the mechanism of representative transformations will be briefly introduced and the prospective in this area will be given.

Key words： allylic substitution; transition metal catalysis; photoredox catalysis; cooperative catalysis

参考文献

[1] (a) Tsuji, J.; Takahashi, H.; Morikawa, M . Tetrahedron Lett. 1965, 6, 4387.
[1] (b) Tsuji, J . Acc. Chem. Res. 1969, 2, 144.
[2] Trost, B. M.; Strege, P. E. J. Am. Chem. Soc. 1977, 99, 1649.
[3] (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
[3] (b) Trost B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921.
[3] (c) Trost, B. M.; Machacek, M. R.; Aponick, A. Acc. Chem. Res. 2006, 39, 747.
[3] (d) Trost, B. M. Org. Process Res. Dev. 2012, 16, 185. 185.
[4] (a) Wang, Y-N.; Lu, L.-Q.; Xiao, W.-J. Chem. Asian J. 2018, 13, 2174.
[4] (b) Tang, H.; Huo, X.; Meng, Q.; Zhang, W. Acta Chim. Sinica 2016, 74, 219 (in Chinese).
[4] (汤淏溟, 霍小红, 孟庆华, 张万斌, 化学学报, 2016, 74, 219.)
[5] (a) Hartwig, J. F.; Stanley, L. M. Acc. Chem. Res. 2010, 43, 1461.
[5] (b) Cheng, Q.; Tu, H. F.; Zheng, C.; Qu, J.-P.; Helmchen, G.; You, S.-L. . Chem Rev. 2019, 119, 1855.
[5] (c) Deng, Y.; Yang, W.; Yang, X.; Yang, D.Chin. J. Org. Chem. 2017, 37, 3039 (in Chinese).
[5] (邓颖颍, 杨文, 杨新, 杨定乔, 有机化学, 2017, 37, 3039.)
[6] (a) Alexakis, A.; B?ckvall, J. E.; Krause, N.; Pàmies, O.; Diéguez, M. . Chem Rev. 2008, 108, 2796.
[6] (b) Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2005, 44, 4435.
[7] Zhang, H.; Gu, Q.; You, S.-L . Chin. J. Org. Chem. 2019, 39, 15 (in Chinese).
[7] ( 张慧君, 顾庆, 游书力 , 有机化学, 2019, 39, 15.)
[8] (a) Turnbull, B. W. H.; Evans, P. A. J. Org. Chem. 2018, 83, 11463.
[8] (b) Thoke, M. B.; Kang, Q. Synthesis 2019, DOI: 10. 1055/s-0037-1611784.
[9] Bruneau, C.; Renaud, J.-L.; Demerseman, B. Chem. Eur. J. 2006, 12, 5178.
[10] (a) Trost, B. M.; Verhoeven, T. R. J. Org. Chem. 1976, 41, 3215.
[10] (b) Matsushita, H.; Negishi, E. J. Chem. Soc. Chem. Commun. 1982, 160.
[10] (c) Lu, Z.; Ma, S. Angew. Chem., Int. Ed. 2008, 47, 258.
[10] (d) Weaver, J. D.; Recio, III, A.; Grenning, A. J.; Tunge, J. A. Chem. Rev. 2011, 111, 1846.
[10] (e) Yu, Y.-N.; X, M.-H. Acta Chim. Sinica 2017, 75, 655 (in Chinese). (于月娜, 徐明华, 化学学报, 2017, 75, 655.)
[10] (f) Transition Metal Catalyzed Enantioselective Allylic Substitution in Organic Synjournal, Ed.: Kazmaier, U., Springer, Heidelberg, 2012.
[11] For reviews on this topic, see: (a) Harutyunyan, S. R.; den Hartog, T.; Geurts, K.; Minnaard, A. J.; Feringa, B. L. Chem. Rev. 2008, 108, 2824.
[11] (b) Alexakis, A.; Backvall, J. E.; Krause, N.; Pa?mies, O.; Die?guez, M . Chem. Rev. 2008, 108, 2796.
[11] (c) Teichert, J. F.; Ferin-ga, B. L. Angew. Chem., Int. Ed. 2010, 49, 2486.
[11] (d) Cherney, A. H.; Kadunce, N. T.; Reisman, S. E. Chem. Rev. 2015, 115, 9587.
[11] (e) Hartwig, J. F.; Pouy, M. J. Top. Organomet. Chem. 2011, 34, 169.
[11] (f) Scha?fer, P.; Sidera, M.; Palacin, T.; Fletcher, S. P. Chem. Commun. 2017, 53, 12499.
[12] (a) Zheng, W.-H.; Zheng, B.-H.; Zhang, Y.; Hou, X.-L. J. Am. Chem. Soc. 2007, 129, 7718.
[12] (b) Trost, B. M.; Thaisrivongs, D. A. J. Am. Chem. Soc. 2008, 130, 14092.
[12] (c) Trost, B. M.; Thaisrivongs, D. A. J. Am. Chem. Soc. 2009, 131, 12056.
[12] (d) Zhang, P.; Brozek, L. A.; Morken, J. P. J. Am. Chem. Soc. 2010, 132, 10686.
[12] (e) Chen, J.-P.; Ding, C.-H.; Liu, W.; Hou, X.-L.; Dai, L.-X. J. Am. Chem. Soc. 2010, 132, 15493.
[12] (f) Zhang, P.; Le, H.; Kyne, R. E.; Morken, J. P. J. Am. Chem. Soc. 2011, 133, 9716.
[12] (g) Trost, B. M.; Thaisrivongs, D. A.; Hartwig, J. J. Am. Chem. Soc. 2011, 133, 12439.
[12] (h) Chen, J.-P.; Peng, Q.; Lei, B.-L.; Hou, X.-L.; Wu, Y.-D. J. Am. Chem. Soc. 2011, 133, 14180.
[12] (i) Brozek, L. A.; Ardolino, M. J.; Morken, J. P. J. Am. Chem. Soc. 2011, 133, 16778.
[12] (j) Ardolino, M. J.; Morken, J. P. J. Am. Chem. Soc. 2014, 136, 7092.
[12] (k) Niyomchon, S.; Audisio, D.; Luparia, M.; Maulide, N. Org. Lett. 2013, 15, 2318.
[12] (l) Misale, A.; Niyomchon, S.; Luparia, M.; Maulide, N. Angew. Chem., Int. Ed. 2014, 53, 7068.
[12] (m) Mao, J.; Zhang, J.; Jiang, H.; Bellomo, A.; Zhang, M.; Gao, Z.; Dreher, S. D.; Walsh, P. J. Angew. Chem., Int. Ed. 2016, 55, 2526.
[12] (n) Murakami, R.; Sano, K.; Iwai, T.; Taniguchi, T.; Monde, K.; Sawamura, M. Angew. Chem., Int. Ed. 2018, 57, 9465.
[13] (a) Butt, N.; Yang, G.; Zhang, W. Chem . Rec. 2016, 16, 2687.
[13] (b) Afewerki, S.; Córdova, A. Chem . Rev. 2016, 116, 13512.
[13] (c) Zhang, M.-M.; Luo, Y.-Y.; Lu, L.-Q.; Xiao, W.-J. Acta Chim. Sinica 2018, 76, 838 (in Chinese).
[13] (张毛毛, 骆元元, 陆良秋, 肖文精, 化学学报, 2018, 76, 838.)
[13] (d) Butt, N. A.; Zhang, W. Chem. Soc. Rev. 2015, 44, 7929.
[13] (e) Fu, J.; Huo, X.; Li, B.; Zhang, W. Org. Biomol. Chem. 2017, 15, 9747.
[14] For reviews on photoredox catalysis, see: (a) Narayanam, J. M. R.; Ste-phenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102.
[14] (b) Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 6828.
[14] (c) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
[14] (d) Dai, X.-J.; Xu, X.-L.; Li, X.-N. Chin. J. Org. Chem. 2013, 33, 2046 (in Chinese).
[14] (戴小军, 许孝良, 李小年, 有机化学, 2013, 33, 2046.)
[14] (e) Schultz, D. M.; Yoon, T. P. Science 2014, 343, 1239176.
[14] (f) Brim-ioulle, R.; Lenhart, D.; Maturi, M. M.; Bach, T. Angew. Chem., Int. Ed. 2015, 54, 3872.
[14] (g) Tan, F.; Xiao, W. Acta Chim. Sinica 2015, 73, 85 (in Chinese).
[14] (谭芬, 肖文精, 化学学报, 2015, 73, 85.)
[14] (h) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075.
[14] (i) Ravelli, D.; Protti, S.; Fagnoni, M. Chem. Rev. 2016, 116, 9850.
[15] For selected examples on palladium metallaphotoredox catalysis, see: (a) Kalyani, D.; McMurtrey, K. B.; Neufeldt, S. R.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 18566.
[15] (b) Neufeldt, S. R.; Sanford, M. S. Adv. Synth. Catal. 2012, 354, 3517.
[15] (c) Zoller, J.; Fabry, D. C.; Ronge, M. A.; Rueping, M. . Angew. Chem., Int. Ed. 2014, 53, 13264.
[15] (d) Mori, K.; Kawashima, M.; Yamashita, H . Chem. Commun. 2014, 50, 14501.
[15] (e) Choi, S.; Chatterjee, T.; Choi, W. J.; You, Y.; Cho, E. J . ACS Catal. 2015, 5, 4796.
[15] (f) Zhou, C.; Li, P.; Zhu, X.; Wang, L . Org. Lett. 2015, 17, 6198.
[15] (g) Cheng, W.-M.; Shang, R.; Yu, H.-Z.; Fu, Y . Chem. Eur. J. 2015, 21, 13191.
[15] (h) Liu, K.; Zou, M.; Lei, A . J. Org. Chem. 2016, 81, 7088.
[15] (i) K?rk?s, M. D.; Bosque, I.; Matsuura, B. S.; Stephenson, C. R. J . Org. Lett. 2016, 18, 5166.
[15] (j) Shimomaki, K.; Murata, K.; Martin, R.; Iwasawa, N . J. Am. Chem. Soc. 2017, 139, 9467.
[15] (k) Kato, S.; Saga, Y.; Kojima, M.; Fuse, H.; Matsunaga, S.; Fukatsu, A.; Kondo, M.; Masaoka, S.; Kanai, M . J. Am. Chem. Soc. 2017, 139, 2204.
[16] For selected examples on nickel metallaphotoredox catalysis, see: (a) Zuo, Z.; Ahneman, D. T.; Chu, L.; Terrett, J. A.; MacMillan, D. W. C. Science 2014, 345, 437.
[16] (b) Tellis, J. C.; Primer, D. N.; Molander, G. A . Science 2014, 345, 433.
[16] (c) Corcé, V.; Chamoreau, L.-M.; Derat, E.; Goddard, J.-P.; Ollivier, C.; Fensterbank, L . Angew. Chem., Int. Ed. 2015, 54, 11414.
[16] (d) Nakajima, K.; Nojima, S.; Nishibayashi, Y . Angew. Chem., Int. Ed. 2016, 55, 14106.
[16] (e) Shaw, M. H.; Shurtleff, V. W.; Terrett, J. A.; Cuthbertson, J. D.; MacMillan, D. W. C . Science. 2016, 352, 1304.
[16] (f) Heitz, D. R.; Tellis, J. C.; Molander, G. A . J. Am. Chem. Soc. 2016, 138, 12715.
[17] For selected examples on copper metallaphotoredox catalysis, see: (a) Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2012, 134, 9034.
[17] (b) Yoo, W.-J.; Tsukamoto, T.; Kobayashi, S. Angew. Chem., Int. Ed. 2015, 54, 6587.
[18] For selected examples on gold metallaphotoredox catalysis, see: (a) Sahoo, B.; Hopkinson, M. N.; Glorius, F. J. Am. Chem. Soc. 2013, 135, 5505.
[18] (b) Shu, X.-Z.; Zhang, M.; He, Y.; Frei, H.; Toste, F. D. J. Am. Chem. Soc. 2014, 136, 5844.
[19] (a) Skubi, K. L.; Blum, T. R.; Yoon, T. P. Chem. Rev. 2016, 116, 10035.
[19] (b) Tellis, J. C.; Kelly, C. B.; Primer, D. N.; Jouffroy, M.; Patel, N. R.; Molander, G. A . Acc. Chem. Res. 2016, 49, 1429..
[19] (c) Twilton, J.; Le, C.; Zhang, P.; Shaw, M. H.; Evans, R. W.; MacMillan, D. W. C . Nature Rev. 2017, 1, 0052.
[19] (d) Wang, C.-S.; Dixneuf, P. H.; Soule?, J.-F . Chem. Rev. 2018, 118, 7532.
[19] (e) Zhou, W.-J.; Zhang, Y.-H.; Gui, Y.-Y.; Sun, L.; Yu, D.-G . Synthesis. 2018, 50, 3359.
[19] (f) Chuentragool, P.; Kurandina, D.; Gevorgyan, V . Angew. Chem., Int. Ed. 2019, DOI: 10. 1002/anie. 201813523.
[20] Lang, S. B.; O’Nele, K. M.; Tunge, J. A. J. Am. Chem. Soc. 2014, 136, 13606.
[21] Lang, S. B.; O’Nele, K. M.; Tunge, J. A. Chem. Eur. J. 2015, 21, 18589.
[22] Xuan, J.; Zeng, T.-T.; Feng,, Z,-J.; Deng, Q.-H.; Chen, J.-R.; Lu, L.-Q.; Xiao, W.-J.; Alper, H. Angew. Chem., Int. Ed. 2015, 54, 1625.
[23] Jennifer, K. Matsui, J. K.; Gutiérrez-Bonet, A.; Rotella, M.; Alam, R.; Gutierrez, O.; Molander, G. A. Angew. Chem., Int. Ed. 2018, 57, 15847.
[24] Thullen, S. M.; Rovis, T. J. Am. Chem. Soc. 2017, 139, 15504.
[25] Zheng, J.; Breit, B. Angew. Chem., Int. Ed. 2019, 58, 3392.
[26] Schwarz, J. L.; Scha?fers, F.; Tlahuext-Aca, A.; Lu?ckemeier, L.; Glorius, F. J. Am. Chem. Soc. 2018, 140, 12705.
[27] For selected examples on asymmetric nickel metallaphotoredox catalysis, see:(a) Zuo, Z.; Cong, H.; Li, W.; Choi, J.; Fu, G. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 138, 1832.
[27] (b) Stache, E. E.; Rovis, T.; Doyle, A. G . Angew. Chem., Int. Ed. 2017, 56, 3679. For selected examples on asymmetric copper metallaphotoredox catalysis, see:
[27] (c) Wang, D.; Zhu, N.; Chen, P.; Lin, Z.; Liu, G . J. Am. Chem. Soc. 2017, 139, 15632.
[27] (d) Sha, W.; Deng, L.; Ni, S.; Mei, H.; Han, J.; Pan, Y . ACS Catal. 2018, 8, 7489.
[28] Zhang, H.-H.; Zhao, J.-J.; Yu, S. J. Am. Chem. Soc. 2018, 140, 16914.
[29] Mitsunuma, H.; Tanabe, S.; Fuse, H.; Ohkubo, K.; Kanai, M . Chem. Sci. 2019, 10, 3459.
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