SIOC English
有机化学
高级检索

有机化学 >

2020 , Vol. 40 >Issue 10: 3196 - 3202

DOI: https://doi.org/10.6023/cjoc202005056

综述与进展

通过过渡金属催化p-不饱和化合物对C—H键的插入反应构建中环

  • 李然 ,
  • 徐学涛 ,
  • 叶萌春
展开
  • a 五邑大学生物科技与大健康学院 广东江门 529020;
    b 南开大学化学学院 元素有机化学国家重点实验室 天津 300071

收稿日期: 2020-05-21

  修回日期: 2020-06-10

  网络出版日期: 2020-06-19

基金资助

国家自然科学基金（Nos.21672107，21871145，91856104）和广东省教育厅（No.2019KZDXM035）资助项目.

收起

Construction of Medium Rings via Transition Metal-Catalyzed Insertion of π-Unsaturated Compounds into C—H Bonds

  • Li Ran ,
  • Xu Xuetao ,
  • Ye Mengchun
Expand
  • a School of Biotechnology and Health Science, Wuyi University, Jiangmen, Guangdong 529020;
    b State Key Laboratory and Institute of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071

Received date: 2020-05-21

  Revised date: 2020-06-10

  Online published: 2020-06-19

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21672107, 21871145, 91856104) and the Department of Education of Guangdong Province (No. 2019KZDXM035).

Fold

摘要

中环（7～9元环）化合物广泛存在于各类具有重要生物活性的天然产物中，发展它们的经济高效的合成方法一直以来受到了密切的关注.总结了近年来通过过渡金属催化的不饱和键对C—H键的插入反应来构建中环化合物的反应.按照使用的金属中间体稳定策略的不同，把这些合成方法分为四类，并从各自的发展、特点、反应类型和反应机理等方面进行了阐述.

关键词： 中环化合物; 过渡金属催化; π-不饱和键; C—H键

本文引用格式

李然 , 徐学涛 , 叶萌春 . 通过过渡金属催化p-不饱和化合物对C—H键的插入反应构建中环[J]. 有机化学, 2020 , 40(10) : 3196 -3202 . DOI: 10.6023/cjoc202005056

Abstract

Medium rings (7~9 membered) widely exist in a variety of natural products that often have important bio-activities, thereby the development of economical and highly efficient synthetic routes to them has received intensive attention. Recent advances on transition metal-catalyzed π-unsaturated compounds inserting into C-H bonds for the construction of medium rings are summarized. According to different strategies that were used to stabilize organometallic intermediates, these methods can be divided into four types, and each of which was described from various aspects including its progress, characteristics, reaction types and mechanisms.

Key words： medium-ring compound; transition metal catalysis; π-unsaturated bond; C-H bond

参考文献

[1] Sakai, K.; Ide, J.; Oda, O.; Nakamura, N. Tetrahedron Lett. 1972, 1287.
[2] Aloise, A. D.; Layton, M. E.; Shair, M. D. J. Am. Chem. Soc. 2000, 122, 12610.
[3] Sato, Y.; Oonishi, Y.; Mori, M. Angew. Chem., Int. Ed. 2002, 41, 1218.
[4] Crépin, D.; Dawick, J.; Aïssa, C. Angew. Chem., Int. Ed. 2010, 49, 620.
[5] Bendorf, H. D.; Colella, C. M.; Dixon, E. C.; Marchetti, M.; Matukonis, A. N.; Musselman, J. D.; Tiley, T. A. Tetrahedron Lett. 2002, 43, 7031.
[6] Bendorf, H. D.; Ruhl, K. E.; Shurer, A. J.; Shaffer, J. B.; Duffin, T. O.; LaBarte, T. L.; Maddock, M. L.; Wheeler, O. W. Tetrahedron Lett. 2012, 53, 1275.
[7] Aïssa, C.; Fürstner, A. J. Am. Chem. Soc. 2007, 129, 14836.
[8] Shen, Z. M.; Khan, H. A.; Dong, V. M. J. Am. Chem. Soc. 2008, 130, 2916.
[9] Shen, Z. M.; Dornan, P. K.; Khan, H. A.; Woo, T. K.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 1077.
[10] Coulter, M. M.; Dornan, P. K.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 6932.
[11] Khan, H. A.; Kou, K. G. M.; Dong, V. M. Chem. Sci. 2011, 2, 407.
[12] Arnold, J. S.; Mwenda, E. T.; Nguyen, H. M. Angew. Chem., Int. Ed. 2014, 53, 3688.
[13] Suggs, J. W. J. Am. Chem. Soc. 1979, 101, 489.
[14] Beletskiy, E. V.; Sudheer, C.; Douglas, C. J. J. Org. Chem. 2012, 77, 5884.
[15] (a) Ding, Z.; Yoshikai, N. Angew. Chem., Int. Ed. 2013, 52, 8574.
(b) Donets, P. A.; Cramer, N. J. Am. Chem. Soc. 2013, 135, 11772.
[16] Donets, P. A.; Cramer, N. Angew. Chem., Int. Ed. 2015, 54, 633.
[17] Diesel, J.; Finogenova, A. M.; Cramer, N. J. Am. Chem. Soc. 2018, 140, 4489.
[18] Diesel, J.; Grosheva, D.; Kodama, S.; Cramer, N. Angew. Chem., Int. Ed. 2019, 58, 11044.
[19] Zhang, W. B.; Yang, X. T.; Ma, J. B.; Su, Z. M.; Shi, S. L. J. Am. Chem. Soc. 2019, 141, 5628.
[20] Cai, Y.; Ye, X. D.; Liu, S.; Shi, S. L. Angew. Chem., Int. Ed. 2019, 58, 13433.
[21] Shen, D.; Zhang, W. B.; Li, Z. Y.; Shi, S. L.; Xu, Y. J. Adv. Synth. Catal. 2020, 362, 1125.
Options
文章导航

/

〈 〉