Chan-Evans-Lam偶联反应研究进展

doi:10.6023/cjoc201702001

有机化学 ›› 2017, Vol. 37 ›› Issue (5): 1069-1087.DOI: 10.6023/cjoc201702001 上一篇下一篇

综述与进展

Chan-Evans-Lam偶联反应研究进展

马小盼, 刘凤萍, 莫冬亮

广西师范大学化学与药学学院省部共建药用资源化学与药物分子工程国家重点实验室桂林 541004

收稿日期:2017-02-02 修回日期:2017-03-21 发布日期:2017-04-13
通讯作者: 莫冬亮 E-mail:moeastlight@mailbox.gxnu.edu.cn
基金资助:
国家自然科学基金（Nos.21562005，21602037）、广西高校百人计划、广西自然科学基金（No.2016GXNSFFA380005）资助项目.

Recent Advances in Chan-Evans-Lam Coupling Reaction

Ma Xiaopan, Liu Fengping, Mo Dongliang

State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University, Guilin 541004

Received:2017-02-02 Revised:2017-03-21 Published:2017-04-13
Contact: 10.6023/cjoc201702001 E-mail:moeastlight@mailbox.gxnu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21562005, 21602037); “Overseas 100 Talents Program” of Guangxi Higher Education, Natural Science Foundation of Guangxi (No. 2016GXNSFFA380005).

文章分享

摘要/Abstract

Chan-Evans-Lam偶联反应在20世纪90年代被发现以后经历了突飞猛进的发展.Chan-Evans-Lam偶联反应作为一类条件温和、高效、官能团兼容性好的偶联方法，不仅被广泛地应用于各种碳-杂键、碳-碳键的形成反应中，也成功地应用于复杂天然产物的全合成中.综述了近5年来Chan-Evans-Lam偶联反应在有机合成中发展的新策略及其在天然产物全合成中的应用.

关键词: 偶联反应, 铜催化, 有机硼试剂, 碳-杂键形成

Chan-Evans-Lam reaction has been served as a powerful cross-coupling reaction in organic synthesis since its discovery in the 1990s owing to the feature of mild reaction conditions, functional group tolerance and open-flask chemistry. Up to now, it has been not only extensively utilized in carbon-heteroatom or carbon-carbon bonds formation, but also successfully applied to synthesize natural products and alkaloids. The new strategies of Chan-Evans-Lam reaction in organic synthesis as well as applications in total synthesis in recent five years are discussesed.

Key words: coupling reaction, copper-catalyzed, organic boron reagents, carbon-heteroatom bond formation

引用此文

马小盼, 刘凤萍, 莫冬亮. Chan-Evans-Lam偶联反应研究进展[J]. 有机化学, 2017, 37(5): 1069-1087.

Ma Xiaopan, Liu Fengping, Mo Dongliang. Recent Advances in Chan-Evans-Lam Coupling Reaction[J]. Chin. J. Org. Chem., 2017, 37(5): 1069-1087.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] See reviews: (a) Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780.
(b) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215.
(c) Mousseau, J. J.; Charette, A. B. Acc. Chem. Res. 2013, 46, 412.
(d) Liu, C.; Liu, D.; Lei, A. Acc. Chem. Res. 2014, 47, 3459.
[2] (a) Tan, M.; Gu, Y.; Luo, X.; Zhang, P. Chin. J. Org. Chem. 2015, 35, 781 (in Chinese). (谭明雄, 顾运琼, 罗旭健, 张培, 有机化学, 2015, 35, 781.)
(b) Zhang, Y.; Nie, B.; Zhang, J. Chin. J. Org. Chem. 2015, 35, 2067 (in Chinese). (张英俊, 聂飚, 张霁, 有机化学, 2015, 35, 2067.)
(c) Lu, Q.;Yi, H.; Lei, A. Acta Chim. Sinica 2015, 73, 1245 (in Chinese). (陆庆全, 易红, 雷爱文, 化学学报, 2015, 73, 1245.)
(d) Zhang, J.; Lu, Q.; Liu, C.; Lei, A. Chin. J. Org. Chem. 2015, 35, 743 (in Chinese). (张剑, 陆庆全, 刘超, 雷爱文, 有机化学, 2015, 35, 743.)
[3] (a) Chan, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933.
(b) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937.
(c) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941.
[4] (a) Ley, S. V.; Thomas, A. W. Angew. Chen., Int. Ed. 2003, 42, 5400.
(b) Thomas, A. W.; Ley, S. V. In Modern Arylation Methods, Ed.: Ackermann, L., Wiley-VCH, Weinherim, 2008, p. 121.
[5] (a) Chan, D. M. T.; Lam, P. Y. S. In Boronic Acids, Ed.: Hall, D. G., Wiley-VCH, Weinheim, 2005, Chapter 5, p. 205.
(b) Li, J. J. In Name Recations: A Collection of Detailed Reaction Mechanisms and Synthetic Applications, 4th ed., Springer, New York, 2009, 102.
[6] (a) King, A. E.; Brunold, T. C.; Stahl, S. S. J. Am. Chem. Soc. 2009, 131, 5044.
(b) King, A. E.; Ryland, B. L.; Brunold, T. C.; Stahl, S. S. Organometallics 2012, 31, 7948.
[7] Larsson, P. F.; Wallentin, C. J.; Norrby, P. O. ChemCatChem 2014, 6, 1277.
[8] Kumar, K. A.; Kannaboina, P.; Jaladanki, C. K.; Bharatam, P. V.; Das, P. ChemistrySelect 2016, 3, 601.
[9] Qiao, J. X.; Lam, P. Y. S. Synlett 2011, 829.
[10] Rao, K. S.; Wu, T. S. Tetrahedron 2012, 68, 7735.
[11] Bruneau, A.; Brion, J. D.; Alami, M.; Messaoudi, S. Chem. Commun. 2013, 49, 8359.
[12] Zhu, X.; Zhang, Q.; Su, W. RSC Adv. 2014, 4, 22775.
[13] Gogoi, A.; Sarmah, G.; Dewan, A.; Bora, U. Tetrahedron Lett. 2014, 55, 31.
[14] Rasheed, S.; Rao, D. N.; Reddy, K. R.; Aravinda, S.; Vishwakarma, R. A.; Das, P. RSC Adv. 2014, 4, 4960.
[15] Yoo, W. J.; Tsukamoto, T.; Kobayashi, S. Angew. Chem., Int. Ed. 2015, 54, 6587.
[16] Rasheed, S.; Rao, D. N.; Das, P. J. Org. Chem. 2015, 80, 9321.
[17] Chen, J.; Natte, K.; Man, N. Y. T.; Stewart, S. G.; Wu, X. F. Tetrahedron Lett. 2015, 56, 4843.
[18] Rizwan, K.; Karakaya, I.; Heitz, D.; Zubair, M.; Rasool, N.; Molander, G. A. Tetrahedron Lett. 2015, 56, 6839.
[19] Mallia, C. J.; Burton, P. M.; Smith, A. M. R.; Walter, G. C.; Baxendale, L. R. Beilstein J. Org. Chem. 2016, 12, 1598.
[20] Roy, S.; Sarma, M. J.; Kashyap, B.; Phukan, P. Chem. Commun. 2016, 52, 1170.
[21] Reddy, A. S.; Reddy, K. R.; Rao, D. N.; Jaladanki, C. K.; Bharatam, P. V.; Lam. P. Y. S.; Das, P. Org. Biomol. Chem. 2017, 15, 801.
[22] Vantourout, J. C.; Law, R. P.; Isidro-Llobet, A.; Atkinson, S. J.; Watson, A. J. B. J. Org. Chem. 2016, 81, 3942.
[23] Krasavin, M. Eur. J. Med. Chem. 2015, 97, 525.
[24] Sarnpitak, P.; Mujumdar, P.; Morisseau, C.; Hwang, C. H.; Hammock, B.; Iurchenko, V.; Zozulya, S.; Gavalas, A.; Geronikaki, A.; Ivanenkov, Y.; Krasavin, M. Eur. J. Med. Chem. 2014, 84, 160.
[25] Darin, D.; Krasavin, M. J. Org. Chem. 2016, 81, 12514.
[26] Onaka, T.; Umemoto, H.; Miki, Y.; Nakamura, A.; Maegawa, T. J. Org. Chem. 2014, 79, 6703.
[27] Boykin, D. W.; Farehat, A. A. Synth. Commun. 2015, 45, 245.
[28] Mandal, P. S.; Kumar, A. V. Synlett 2016, 27, 1408.
[29] Garnier, T.; Sakly, R.; Danel, M.; Chassaing, S.; Pale, P. Synthesis 2017, 49, 1223.
[30] Rao, D. N.; Rasheed, S.; Vishwakarma, R. A.; Das, P. Chem. Commun. 2014, 50, 12911.
[31] Beyer, A.; Castanheiro, T.; Busca, P.; Prestat, G. ChemCatChem 2015, 7, 2433.
[32] Rao, D. N.; Rasheed, S.; Kumar, K. A.; Reddy, A. S.; Das, P. Adv. Synth. Catal. 2016, 358, 2126.
[33] Kumar, K. A.; Kannaboina, P.; Rao, D. N.; Das, P. Org. Biomol. Chem. 2016, 14, 8989.
[34] Nandi, G. C.; Kota, S. R.; Govender, T.; Kruger, H. G.; Arvidsson, P. I. Tetrahedron 2014, 70, 5428.
[35] Moon, S. Y.; Nam, J.; Rathwell, K.; Kim, W. S. Org. Lett. 2014, 16, 338.
[36] You, C.; Yao, F.; Yan, T.; Cai, M. RSC Adv. 2016, 6, 43605.
[37] Mo, D.-L.; Anderson, L. L. Angew. Chem., Int. Ed. 2013, 52, 6722.
[38] Mo, D.-L.; Wink, D. A.; Anderson, L. L. Org. Lett. 2012, 14, 5180.
[39] Kontokosta, D.; Mueller, D. S.; Mo, D.-L.; Pace, W. H.; Simpson, R. A.; Anderson, L. L. Beilstein J. Org. Chem. 2015, 11, 2097.
[40] Ohata, J.; Minus, M. B.; Abernathy, M. E.; Ball, Z. T. J. Am. Chem. Soc. 2016, 138, 7472.
[41] Rossi, S. A.; Shimkin, K. W.; Xu, Q.; Mori-Quiroz, L. M.; Watson, D. A. Org. Lett. 2013, 15, 2314.
[42] Racine, E.; Monnier, F.; Vors, J.-P.; Taillefer, M. Chem. Commun. 2013, 49, 7412.
[43] (a) Tabolin, A. A.; Ioffe, S. L. Chem. Rev. 2014, 114, 5426.
(b) Shi, W.-M.; Ma, X.-P.; Su, G.-F.; Mo, D.-L. Org. Chem. Front. 2016, 3, 116.
[44] Mondal, M.; Sarmah, G.; Gogoi, K.; Bora, U. Tetrahedron Lett. 2012, 53, 6219.
[45] Mulla, S. A. R.; Chavan, S. S.; Inamdar, S. M.; Pathan, M. Y.; Shaikh, T. M. Y. Tetrahedron Lett. 2014, 55, 5327.
[46] Medda, A.; Pal, G.; Singha, R.; Hossain, T.; Saha, A.; Das, A, R. Synth. Commun. 2013, 43, 169.
[47] ?ermak, J. K.; Církva, V. Tetrahedron Lett. 2014, 55, 4185.
[48] Wang, R.; Wang, L.; Zhang, K.; Li, J.; Zou, D.; Wu, Y.; Wu, Y. Tetrahedron Lett. 2015, 56, 4815.
[49] Khatib, M. E.; Molander, G. A. Org. Lett. 2014, 16, 4944.
[50] Marcum, J. S.; McGarry, K. A.; Ferber, C. J.; Clark, T. B. J. Org. Chem. 2016, 81, 7963.
[51] Huang, F.; Quach, T. D.; Batey, R. A. Org. Lett. 2013, 15, 3150.
[52] Patil, A. S.; Mo, D.-L.; Wang, H. Y.; Mueller, D. S.; Anderson, L. L. Angew. Chem., Int. Ed. 2012, 51, 7799.
[53] Wang, H. Y.; Anderson, L. L. Org. Lett. 2013, 15, 3362.
[54] Kontokosta, D.; Mueller, D. S.; Wang, H. Y.; Anderson, L. L. Org. Lett. 2013, 15, 4830.
[55] Xu, H. J.; Zhao, Y. Q.; Feng, T.; Feng, Y. S. J. Org. Chem. 2012, 77, 2878.
[56] Lin, Y.; Cai, M.; Fang, Z.; Zhao, H. Tetrahedron 2016, 72, 3335.
[57] Qian, Z.; Ge, N.; Jiang, X. Chem. Commun. 2015, 51, 10295.
[58] Xiao, X.; Feng, M.; Jiang, X. Angew. Chem., Int. Ed. 2016, 55, 14121.
[59] Koley, S.; Chowdhury, S.; Chanda, T.; Ramulu, B. J.; Anand, N.; Singh, M. S. Eur. J. Org. Chem. 2015, 409.
[60] Xu, J.; Xiao, B.; Xie, C. Q.; Luo, D. F.; Liu, L.; Fu, Y. Angew. Chem., Int. Ed. 2012, 51, 12551.
[61] Moon, P. J.; Halperin, H. M.; Lundgren, R. J. Angew. Chem., Int. Ed. 2016, 55, 1894.
[62] Moon, P. J.; Yin, S. K.; Lundgren, R. J. J. Am. Chem. Soc. 2016, 138, 13826.
[63] Li, H.; Tsu, C.; Blackburn, C.; Li, G.; Hales, P.; Dick, L.; Bogyo, M. J. Am. Chem. Soc. 2014, 136, 13562.
[64] Feng, Y.; Holte, D.; Zoller, J.; Umemiya, S.; Simke, L. R.; Baran. P. S. J. Am. Chem. Soc. 2015, 137, 10160.

Chan-Evans-Lam偶联反应研究进展

Recent Advances in Chan-Evans-Lam Coupling Reaction

PDF

可视化

被引次数

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 15

编辑推荐

相关统计

本文评价

[1]	陈雯雯, 张琴, 张松月, 黄芳芳, 张馨尹, 贾建峰. 无光催化剂条件下可见光诱导炔基碘和亚磺酸钠偶联反应[J]. 有机化学, 2024, 44(2): 584-592.
[2]	宋晓, 卿晶, 黎君, 贾雪雷, 吴福松, 黄均荣, 金剑, 游恒志. 铜催化格氏试剂的不对称烯丙基烷基化连续流反应[J]. 有机化学, 2023, 43(9): 3174-3179.
[3]	陈祖佳, 宇世伟, 周永军, 李焕清, 邱琪雯, 李妙欣, 汪朝阳. BF₃•OEt₂作为催化剂与合成子在有机合成中的应用进展[J]. 有机化学, 2023, 43(9): 3107-3118.
[4]	陆晓雨, 孙晓梅, 钮亚琴, 王俊超, 殷文婧, 高梦婷, 刘孜, 韦正桓, 陶庭骅. 铜催化氟代丙烯酸与氧杂吖丙啶的脱羧交叉偶联反应[J]. 有机化学, 2023, 43(6): 2110-2119.
[5]	鲍志成, 李慕尧, 王剑波. 铜催化芳基重氮乙酸酯与双[(频哪醇)硼基]甲烷的偶联反应[J]. 有机化学, 2023, 43(5): 1808-1814.
[6]	李春生, 连晓琪, 陈莲芬. 铜催化亚砜叶立德与邻苯二胺[4＋2]环加成反应[J]. 有机化学, 2023, 43(4): 1492-1498.
[7]	刘洋, 黄翔, 王敏, 廖建. 铜催化环酮亚胺与β,γ-不饱和N-酰基吡唑不对称Mannich-Type反应[J]. 有机化学, 2023, 43(4): 1499-1509.
[8]	刘春阳, 李燕, 张前. 铜催化环状烯烃烯丙位C(sp³)—H磺酰化反应研究[J]. 有机化学, 2023, 43(3): 1091-1101.
[9]	刘宁, 爨晓丹, 李慧, 段希焱. 烯胺酮α-官能团化反应的研究进展[J]. 有机化学, 2023, 43(2): 602-621.
[10]	韩彪, 李维双, 陈舒晗, 张泽浪, 赵雪, 张瑶瑶, 朱磊. 铜催化不饱和化合物硅加成反应的研究进展[J]. 有机化学, 2023, 43(2): 555-572.
[11]	马彪, 章淼淼, 李占宇, 彭进松, 陈春霞. 无过渡金属催化的Suzuki-Type交叉偶联反应研究进展[J]. 有机化学, 2023, 43(2): 455-470.
[12]	刘婷婷, 胡宇才, 沈安. 亚胺配体协同氮杂环卡宾钯配合物催化碳碳偶联反应的作用机制[J]. 有机化学, 2023, 43(2): 622-628.
[13]	秦思凝. 芳香卤代物C—S偶联反应的研究进展[J]. 有机化学, 2023, 43(11): 3761-3783.
[14]	许力, 吕兰兰, 王香善. 铜催化烯醇硅醚与芳基亚磺酸钠合成β-酮砜的研究[J]. 有机化学, 2023, 43(10): 3644-3651.
[15]	马伟源, 戴惠芳, 亢少林, 张天麟, 舒兴中. 芳基乙烯基硅烷与芳基卤代物的Hiyama偶联反应[J]. 有机化学, 2023, 43(10): 3614-3622.