Recent Advances in Ni-Catalyzed Allylic Substitution Reactions

doi:10.6023/cjoc201809037

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 15-27.DOI: 10.6023/cjoc201809037 Previous Articles Next Articles

Special Issue: 庆祝陈庆云院士九十华诞

Reviews

镍催化的烯丙基取代反应研究进展

张慧君^a, 顾庆^b, 游书力^a,b

a 华东理工大学化学与分子工程学院上海 200237;
b 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032

收稿日期:2018-09-28 修回日期:2018-09-28 发布日期:2018-10-26
通讯作者: 顾庆, 游书力 E-mail:qinggu@sioc.ac.cn;slyou@sioc.ac.cn
基金资助:
国家重点研发计划（No.2016YFA0202900）、国家重点基础研究发展计划（973计划，No.2015CB856600）、国家自然科学基金（Nos.21332009，21572250，21572252）、中国科学院（Nos.XDB20000000，QYZDY-SSW-SLH012）资助项目.

Recent Advances in Ni-Catalyzed Allylic Substitution Reactions

Zhang Huijun^a, Gu Qing^b, You Shuli^a,b

a School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237;
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2018-09-28 Revised:2018-09-28 Published:2018-10-26
Contact: 10.6023/cjoc201809037 E-mail:qinggu@sioc.ac.cn;slyou@sioc.ac.cn
Supported by:
Project supported by the National Key R&D Program of China (No. 2016YFA0202900), the National Basic Research Program of China (973 Program, No. 2015CB856600), the National Natural Science Foundation of China (Nos. 21332009, 21572250, 21572252), and the Chinese Academy Sciences (Nos. XDB20000000, QYZDY-SSW-SLH012).

Transition-metal catalyzed allylic substitution reaction is an important approach for constructing carbon-carbon bond and carbon-heteroatom bond. Due to its cheapness, easy access, and wide applicability in organic synthesis, nickel has attracted intense attention. Over the past 50 years, nickel-catalyzed allylic substitution reactions have been extensively studied. The progresses on nickel-catalyzed allylic substitution reactions and their applications in organic synthesis are summarized according to bond formation and nucleophilic reagent.

Key words: allylic substitution, asymmetric catalysis, nickel, transition metal

Cite this article

Zhang Huijun, Gu Qing, You Shuli. Recent Advances in Ni-Catalyzed Allylic Substitution Reactions[J]. Chin. J. Org. Chem., 2019, 39(1): 15-27.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] For selected reviews, see:(a) Helmchen, G. J. Organomet. Chem. 1999, 576, 203.
(b) Tenaglia, A.; Heumann, A. Angew. Chem., Int. Ed. 1999, 38, 2180.
(c) Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1.
(d) Kazmaier, U. Curr. Org. Chem. 2003, 7, 317.
(e) Trost, B. M. J. Org. Chem. 2004, 69, 5813.
(f) Jensen, T.; Fristrup, P. Chem.-Eur. J. 2009, 15, 9632.
(g) Milhau, L.; Guiry, P. J. Top. Organomet. Chem. 2012, 38, 95.
[2] For selected reviews, see:(a) Takeuchi, R.; Kezuka, S. Synthesis 2006, 3349.
(b) Helmchen, G.; Dahnz, A.; Dübon, P.; Schelwies, M.; Weihofen, R. Chem. Commun. 2007, 675.
(c) Hartwig, J. F.; Stanley, L. M. Acc. Chem. Res. 2010, 43, 1461.
(d) Hartwig, J. F.; Pouy, M. J. Top. Organomet. Chem. 2011, 34, 169.
(e) Liu, W.-B.; Xia, J.-B.; You, S.-L. Top. Organomet. Chem. 2012, 38, 155.
(f) Tosatti, P.; Nelson, A.; Marsden, S. P. Org. Biomol. Chem. 2012, 10, 3147.
(g) Helmchen, G. In Molecular Catalysis, Eds.:Gade, L. H.; Hofmann, P., Wiley-VCH, Weinheim, 2014, pp. 235~254.
(h) Zhuo, C.-X.; Zheng, C.; You, S.-L. Acc. Chem. Res. 2014, 47, 2558.
(i) Hethcox, J. C.; Shockley, S. E.; Stoltz, B. M. ACS Catal. 2016, 6, 6207.
(j) Qu, J.; Helmchen, G. Acc. Chem. Res. 2017, 50, 2539.
[3] For selected reviews, see:(a) Evans, P. A.; Nelson, J. D. J. Am. Chem. Soc. 1998, 120, 5581.
(b) Selvakumar, K.; Valentini, M.; Pregosin, P. S.; Albinati, A. Organometallics 1999, 18, 4591.
(c) Hayashi, T.; Okada, A.; Suzuka, T.; Kawatsura, M. Org. Lett. 2003, 5, 1713.
(d) Ashfeld, B. L.; Miller, K. A.; Martin, S. F. Org. Lett. 2004, 6, 1321.
[4] For selected reviews, see:(a) Minami, I.; Shimizu, I.; Tsuji, J. J. Organomet. Chem. 1985, 296, 269.
(b) Zhang, S.-W.; Mitsudo, T.; Kondo, T.; Watanabe, Y. J. Organomet. Chem. 1993, 450, 197.
(c) Matsushima, Y.; Onitsuka, K.; Kondo, T.; Mitsudo, T.; Takahashi, S. J. Am. Chem. Soc. 2001, 123, 10405.
(d) Trost, B. M.; Fraisse, P. L.; Ball, Z. T. Angew. Chem., Int. Ed. 2002, 41, 1059.
(e) Mbaye, M. D.; Demerseman, B.; Renaud, J.-L.; Toupet, L.; Bruneau, C. Angew. Chem., Int. Ed. 2003, 42, 5066.
(f) Hermatschweiler, R.; Fernandez, I.; Breher, F.; Pregosin, P. S.; Veiros, L. F.; Calhorda, M. J. Angew. Chem., Int. Ed. 2005, 44, 4397.
(g) Kawatsura, M.; Ata, F.; Wada, S.; Hayase, S.; Uno, H.; Itoh, T. Chem. Commun. 2007, 298.
[5] For selected reviews, see:(a) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
(b) Ho, C.-Y.; Schleicher, K. D.; Chan, C.-W.; Jamison, T. F. Synlett 2009, 2565.
(c) Pigge, F. C. Synthesis 2010, 1745.
[6] Henrion, M.; Ritleng, V.; Chetcuti, M. J. ACS Catal. 2015, 5, 1283.
[7] For selected examples, see:(a) Schaub, T.; Backes, M.; Radius, U. J. Am. Chem. Soc. 2006, 128, 15964.
(b) Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.; Zhang, N.; Resmerita, A.-M.; Garg, N. K.; Percec, V. Chem. Rev. 2011, 111, 1346.
(c) Li, B.-J.; Yu, D.-G.; Sun, C.-L.; Shi, Z.-J. Chem.-Eur. J. 2011, 17, 1728.
(d) Tobisu, M.; Xu, T.; Shimasaki, T.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 19505.
[8] Chuit, C.; Felkin, H.; Frajerman, C.; Roussi, G.; Swierczewski, G. Chem. Commun. 1968, 1604.
[9] Felkin, H.; Swierczewski, G. Tetrahedron Lett. 1972, 15, 1433.
[10] Felkin, H.; Joly-Goudket, M.; Davies, S. G. Tetrahedron Lett. 1981, 22, 1157.
[11] Consiglio, G.; Morandini, F.; Piccolol, O. Helv. Chim. Acta 1980, 63, 987.
[12] Consiglio, G.; Morandini, F.; Piccolo, O. J. Chem. Soc., Chem. Commun. 1983, 112.
[13] Consiglio, G.; Piccolo, O.; Roncetti, L.; Morandini, F. Tetrahedron 1986, 42, 2043.
[14] Hiyama, T.; Wakasa, N. Tetrahedron Lett. 1985, 26, 3259.
[15] Nomura, N.; RajanBabu, T. V. Tetrahedron Lett. 1997, 38, 1713.
[16] Gomez-Bengoa, E.; Heron, N. M.; Didiuk, M. T.; Luchaco, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 7649.
[17] Chung, K.-G.; Miyake, Y.; Uemura, S. J. Chem. Soc., Perkin Trans. 12000, 2725.
[18] Trost, B. M.; Spagnol, M. D. J. Chem. Soc., Perkin Trans. 11995, 2083.
[19] (a) Kobayashi, Y.; Ikeda, E. J. Chem. Soc., Chem. Commun. 1994, 1789.
(b) Kobayashi, Y.; Tokoro, Y.; Watatani, K. Eur. J. Org. Chem. 2000, 3825.
(c) Kobayashi, Y.; Watatani, K.; Kikori, Y.; Mizojiri, R. Tetrahedron Lett. 1996, 37, 6125.
(d) Kobayashi, Y.; Takahisa, E.; Usmani, S. B. Tetrahedron Lett. 1998, 39, 597.
(e) Kobayashi, Y.; Takahisa, E.; Usmani, S. B. Tetrahedron Lett. 1998, 39, 601.
(f) Jimenez-Aquino, A.; Flegeau, E. F.; Schneider, U.; Kobayashi, S. Chem. Commun. 2011, 47, 9456.
[20] Chung, K.-G.; Miyake, Y.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 15.
[21] Chen, H.; Deng, M.-Z. J. Organomet. Chem. 2000, 603, 189.
[22] (a) Shields, J. D.; Ahneman, D. T.; Graham, T. J. A.; Doyle, A. G. Org. Lett. 2014, 16, 142.
(b) Sylvester, K. T.; Wu, K.; Doyle, A. G. J. Am. Chem. Soc. 2012, 134, 16967.
(c) Graham, T. J. A.; Shields, J. D.; Doyle, A. G. Chem. Sci. 2011, 2, 980.
[23] Srinivas, H. D.; Zhou, Q.; Watson, M. P. Org. Lett. 2014, 16, 3596.
[24] Nazari, S. H.; Bourdeau, J. E.; Talley, M. R.; Valdivia-Berroeta, G. A.; Smith, S. J.; Michaelis, D. J. ACS Catal. 2018, 8, 86.
[25] Chau, S. T.; Lutz, J. P.; Wu, K.; Doyle, A. G. Angew. Chem., Int. Ed. 2013, 52, 9153.
[26] For some recent examples synthesis of biologically active 4-piperidines, see:(a) Tawara, J. N.; Lorenz, P. F.; Stermitz, R. J. Nat. Prod. 1999, 62, 321.
(b) Watson, P. S.; Jiang, B.; Scott, B. Org. Lett. 2000, 2, 3679.
(c) Brooks, C. A.; Comins, D. L. Tetrahedron Lett. 2000, 41, 3551.
[27] (a) Wu, D.; Wang, Z.-X. Org. Biomol. Chem. 2014, 12, 6414.
(b) Wu, D.; Tao, J.-L.; Wang, Z.-X. Org. Chem. Front. 2015, 2, 265.
[28] Tao, J.-L.; Yang, B.; Wang, Z.-X. J. Org. Chem. 2015, 80, 12627.
[29] Yang, B.; Wang, Z.-X. J. Org. Chem. 2017, 82, 4542.
[30] Bricout, H.; Carpentier, J.-F.; Mortreux, A. J. Chem. Soc., Chem. Commun. 1995, 1863.
[31] Bricout, H.; Carpentier, J.-F.; Mortreux, A. Tetrahedron Lett. 1996, 37, 6105.
[32] Sha, S.-C.; Jiang, H.; Mao, J.; Bellomo, A.; Jeong, S. A.; Walsh, P. J. Angew. Chem., Int. Ed. 2016, 55, 1070.
[33] For selected examples, see:(a) Lu, X.; Lu, L. J. Organomet. Chem. 1986, 307, 285.
(b) Lu, X.; Lu, L.; Sun, J. J. Mol. Catal. 1987, 41, 245.
(c) Lu, X.; Jiang, X.; Tao, X. J. Organomet. Chem. 1988, 344, 109.
[34] For selected examples, see:(a) Starý, I.; Stará, I. G.; Kocovský, P. Tetrahedron Lett. 1993, 34, 179.
(b) Starý, I.; Stará, I. G.; Kocovský, P. Tetrahedron 1994, 50, 529.
(c) Tamaru, Y.; Horino, Y.; Araki, M.; Tanaka, S.; Kimura, M. Tetrahedron Lett. 2000, 41, 5705.
(d) Takacs, J. M.; Jiang, X.-T.; Leonov, A. P. Tetrahedron Lett. 2003, 44, 7075.
(e) Kimura, M.; Mukai, R.; Tanigawa, N.; Tanaka, S.; Tamaru, Y. Tetrahedron 2003, 59, 7767.
[35] Itoh, K.; Hamaguchi, N.; Miura, M.; Nomura, M. J. Chem. Soc., Perkin Trans. 11992, 1, 2833.
[36] Kita, Y.; Kavthe, R. D.; Oda, H.; Mashima, K. Angew. Chem., Int. Ed. 2016, 55, 1098.
[37] Blieck, R.; Azizi, M. S.; Mifleur, A.; Roger, M.; Persyn, C.; Sauthier, M.; Bonin, H. Eur. J. Org. Chem. 2016, 1194.
[38] Bernhard, Y.; Thomson, B.; Ferey, V.; Sauthier, M. Angew. Chem., Int. Ed. 2017, 56, 7460.
[39] For selected examples, see:(a) Kimura, M.; Horino, Y.; Mukai, R.; Tanaka, S.; Tamaru, Y. J. Am. Chem. Soc. 2001, 123, 10401.
(b) Kimura, M.; Shimizu, M.; Shibata, K.; Tazoe, M.; Tamaru, Y. Angew. Chem., Int. Ed. 2003, 42, 3392.
[40] Jiang, G.; List, B. Adv. Synth. Catal. 2011, 353, 1667.
[41] For selected examples, see:(a) Ibrahem, I.; Clrdova, A. Angew. Chem., Int. Ed. 2006, 45, 1952.
(b) Mukherjee, S.; List, B. J. Am. Chem. Soc. 2007, 129, 11336.
(c) Jiang, G.; List, B. Angew. Chem., Int. Ed. 2011, 50, 9471.
[42] Wang, J.; Wang, P.; Wang, L.; Li, D.; Wang, K.; Wang, Y.; Zhu, H.; Yang, D.; Wang, R. Org. Lett. 2017, 19, 4826.
[43] Ngamnithiporn, A.; Jette, C. I.; Bachman, S.; Virgil, S. C.; Stoltz, B. M. Chem. Sci. 2018, 9, 2547.
[44] Cui, D.-M.; Hashimoto, N.; Ikeda, S.-I.; Sato, Y. J. Org. Chem. 1995, 60, 5752.
[45] For selected examples, see:(a) Ng, S.-S.; Ho, C.-Y.; Schleicher, K. D.; Jamison, T. F. Pure Appl. Chem. 2008, 80, 929.
(b) Ogoshi, S.; Haba, T.; Ohashi, M. J. Am. Chem. Soc. 2009, 131, 10350.
[46] Matsubara, R.; Jamison, T. F. J. Am. Chem. Soc. 2010, 132, 6880.
[47] Matsubara, R.; Gutierrez, A. C.; Jamison, T. F. J. Am. Chem. Soc. 2011, 133, 19020.
[48] For selected examples, see:(a) Miller, J. A.; Negishi, E.-I. Tetrahedron Lett. 1984, 25, 5863.
(b) Sabarre, A.; Love, J. Org. Lett. 2008, 10, 3941.
[49] For selected examples, see:(a) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4992.
(b) Kamlage, S.; Sefkow, M.; Peter, M. G. J. Org. Chem. 1999, 64, 2938.
(c) Zhang, S.; Marshall, D.; Liebeskind, L. S. J. Org. Chem. 1999, 64, 2796.
(d) Perez, I.; Sestelo, J. P.; Sarandeses, L. A. J. Am. Chem. Soc. 2001, 123, 4155.
[50] Standley, E. A.; Jamison, T. F. J. Am. Chem. Soc. 2013, 135, 1585.
[51] Furukawa, J.; Kui, J.; Yamamoto, K.; Tojo, T. Tetrahedron 1973, 29, 3149.
[52] Moberg, C. Tetrahedron Lett. 1980, 21, 4539.
[53] Yamamoto, T.; Ishizu, J.; Yamamoto, A. J. Am. Chem. Soc. 1981, 103, 6863.
[54] Bricout, H.; Carpentier, J.-F.; Mortreux, A. Tetrahedron 1998, 54, 1073.
[55] Berkowitz, D. B.; Maiti, G. Org. Lett. 2004, 6, 2661.
[56] Kita, Y.; Sakaguchi, H.; Hoshimoto, Y.; Nakauchi, D.; Nakahara, Y.; Carpentier, J.-F.; Ogoshi, S.; Mashima, K. Chem.-Eur. J. 2015, 21, 14571.
[57] For selected examples, see:(a) Brunkan, N. M.; Jones, W. D. J. Organomet. Chem. 2003, 683, 77.
(b) Brunkan, N. M.; Brestensky, D. M.; Jones, W. D. J. Am. Chem. Soc. 2004, 126, 3627.
(c) Chaumonnot, A.; Lamy, F.; Sabo-Etienne, S.; Donnadieu, B.; Chaudret, B.; Barthelat, J.-C.; Galland, J.-C. Organometallics 2004, 23, 3363.
(d) Acosta-Ramírez, A.; Muñoz-Hernández, M.; Jones, W. D.; Garcia, J. J. J. Organomet. Chem. 2006, 691, 3895.
[58] Azizi, M. S.; Edder, Y.; Karim, A.; Sauthier, M. Eur. J. Org. Chem. 2016, 3796.
[59] Cuvigny, T.; Julia, M. J. Organomet. Chem. 1983, 250, C21.
[60] Yatsumonji, Y.; Ishida, Y.; Tsubouchi, A.; Takeda, T. Org. Lett. 2007, 9, 4603.

镍催化的烯丙基取代反应研究进展

Recent Advances in Ni-Catalyzed Allylic Substitution Reactions

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Shuang Yang, Xinqiang Fang. Kinetic Resolutions Enabled by N-Heterocyclic Carbene Catalysis: An Update [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 448-480.
[2]	Wanting Chen, Xiongwei Zhong, Jiale Xing, Changshu Wu, Yang Gao. Progress in Asymmetric Catalytic Synthesis of C—N Axis Chiral Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 349-377.
[3]	Jie Liu, Feng Han, Shuangyan Li, Tianyu Chen, Jianhui Chen, Qing Xu. Transition Metal-Free Selective Aerobic Olefination of Methyl N-Heteroarenes with Alcohols [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 573-583.
[4]	Quanbin Jiang. Progress in Synthesis of Axially Chiral Compounds through aza-Vinylidene o-Quinone Methide Intermediates [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 159-172.
[5]	Hao Qin, Chuanjin Hou, Dinghua Liang, Xinwei He, Ling Li, Xiangping Hu. Chiral P,N,N-Ligands for Pd-Catalyzed Asymmetric Allylic Substitutions [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 282-290.
[6]	Hongqiong Zhao, Miao Yu, Dongxue Song, Qi Jia, Yingjie Liu, Yubin Ji, Ying Xu. Progress on Decarboxylation and Hydroxylation of Carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 70-84.
[7]	Chun-Xia Cheng, Lu-Ping Wu, Feng Sha, Xin-Yan Wu. Enantioselective Vinylogous Allylic Alkylation of Coumarins with Morita-Baylis-Hillman Carbonates Catalyzed by Chiral Phosphine-Amide [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3188-3195.
[8]	Wenfang Wang. Recent Progress in Transition-Metal-Catalyzed Asymmetric C—H Borylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3146-3166.
[9]	Xiaoyang Gao, Ruirui Zhai, Xun Chen, Shuojin Wang. Recent Progress in C—H Bond Activation Reaction with Vinylene Carbonate [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3119-3134.
[10]	Sifan Dong, Haolong Li, Yuan Qin, Shiming Fan, Shouxin Liu. Research Progress of Amino Acids as Transient Directing Groups in C—H Bond Activation Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2351-2367.
[11]	Zhongrong Xu, Jieping Wan, Yunyun Liu. Transition Metal-Free C—H Thiocyanation and Selenocyanation Based on Thermochemical, Photocatalytic and Electrochemical Process [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2425-2446.
[12]	Cheng Luo, Yanli Yin, Zhiyong Jiang. Recent Advances in Asymmetric Synthesis of P-Chiral Phosphine Oxides [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1963-1976.
[13]	Xiaojing Hu, Feixiang Guo, Runqing Zhu, Bingqi Zhou, Tao Zhang, Lizhen Fang. Synthesis of p-Alkoxy Phenol and Its Application after Dearomatization [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2239-2244.
[14]	Jiao Qin, Jie Chen, Yan Su. Synthesis of 2,2,6,6-Tetramethylpiperidin-1-yl-2-(2-cyanophenyl)-acetate by Transition Metal-Free Radical Cleavage Reaction from α-Bromoindanone [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2171-2177.
[15]	Yangyang Chu, Zhaobin Han, Kuiling Ding. Progresses in the Application of Kinetic Resolution in Transition Metal Catalyzed Asymmetric (Transfer) Hydrogenation [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1934-1951.