Advances on the Metallocarbene Formation Reactions Based on Triazole Derivatives

doi:10.6023/cjoc201601042

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (7): 1555-1563.DOI: 10.6023/cjoc201601042 Previous Articles Next Articles

Reviews

基于三氮唑类化合物的金属卡宾形成反应研究进展

黄家翩, 周豪, 陈知远

江西师范大学化学化工学院功能有机小分子教育部重点实验室南昌 330022

收稿日期:2016-01-29 修回日期:2016-02-28 发布日期:2016-03-18
通讯作者: 陈知远 E-mail:zchen@jxnu.edu.cn
基金资助:
国家自然科学基金（No.21462022）资助项目.

Advances on the Metallocarbene Formation Reactions Based on Triazole Derivatives

Huang Jiapian, Zhou Hao, Chen Zhiyuan

Key Laboratory of Functional Small Organic Molecules, Ministry of Education, College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022

Received:2016-01-29 Revised:2016-02-28 Published:2016-03-18
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21462022).

Carbenes are very useful key intermediates in organic synthesis, which generally display high reactivity in chemical transformations. Metallocarbenes can be regarded as metal stabilized organic carbenes. The research progress of the metallocarbene formation and the related reactions based on triazole compounds are reviewed in this work. The Rh^II-catalyzed metallocarbenes derived from N-sulfonyl-1,2,3-triazoles, as well as the subsequent insertion reactions into other reaction systems to generate new C-C or C-hetero bonds, are specially focused.

Key words: transition-metal-catalysis, metallocarbenes, triazole compounds, carbo and heterocyclic compounds

Cite this article

Huang Jiapian, Zhou Hao, Chen Zhiyuan. Advances on the Metallocarbene Formation Reactions Based on Triazole Derivatives[J]. Chin. J. Org. Chem., 2016, 36(7): 1555-1563.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Fischer, E. O. Angew. Chem., Int. Ed. 1974, 86, 651.
(b) Schrock, R. R. Acc. Chem. Soc. 1979, 12, 98.
[2] Ma, S. M. Metal-mediated Modern Organic Synthesis, Guangdong Science and Technology Press, Guangzhou, 2001 (in Chinese). (麻生明, 金属参与的现代有机合成反应, 广东科技出版社, 广州, 2001.)
[3] (a) Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861.
(b) Davies, H. M. L.; Alford, J. Chem. Soc. Rev. 2014, 43, 5151.
[4] Chuprakov, S.; Hwang, F. W.; Gevorgyan, V. Angew. Chem., Int. Ed. 2007, 46, 4757.
[5] Horneff, T.; Chuprakov, S.; Chernyak, N.; Gevorgyan, V.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 14972.
[6] For a review, see: Chattopadhyay, B.; Gevorgyan, V. Angew. Chem., Int. Ed. 2012, 51, 862.
[7] Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417.
[8] (a) Horneff, T.; Chuprakov, S.; Chernyak, N.; Gevorgyan, V.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 14972.
(b) Chuprakov, S.; Kwok, S. W.; Zhang, L.; Lercher, L.; Fokin, V. V. J. Am. Chem. Soc. 2009, 131, 18034.
[9] Grimster, N.; Zhang, L.; Fokin, V. V. J. Am. Chem. Soc. 2010, 132, 2510.
[10] Chuprakov, S.; Kwok, S. W.; Zhang, L; Lercher, L.; Fokin, V. V. J. Am. Chem. Soc. 2009, 131, 18034.
[11] For recent application examples, see: (a) Davies, H. M. L.; Nagashima, T.; Klino, J. L. Org. Lett. 2000, 2, 823.
(b) Davies, H. M. L.; Lee, G. H. Org. Lett. 2004, 6, 1233.
(c) Davies, H. M. L.; Coleman, M. G.; Ventura, D. L. Org. Lett. 2007, 9, 4971.
[12] (a) Reddy, R. P.; Lee, G. H.; Davies, H. M. L. Org. Lett. 2006, 8, 3437.
(b) Denton, J. R.; Sukumaran, D.; Davies, H. M. L. Org. Lett. 2007, 9, 2625.
(c) Denton, J. R.; Davies, H. M. L. Org. Lett. 2009, 11, 787.
[13] For cyclopropanation, see:
(a) DeAngelis, A.; Dmitrenko, O.; Yap, G. P. A.; Fox, J. M. J. Am. Chem. Soc. 2009, 131, 7230.
For C—H insertions, see:
(b) Minami, K.; Saito, H.; Tsutsui, H.; Nambu, H.; Anada, M.; Hashimoto, S. Adv. Synth. Catal. 2005, 347, 1483.
(c) Tsutsui, H.; Yamaguchi, Y.; Kitagaki, S.; Nakamura, S.; Anada, M.; Hashimoto, S. Tetrahedron 2003, 14, 817.
(d) Saito, H.; Oishi, H.; Kitagaki, S.; Nakamura, S.; Anada, M.; Hashimoto, S. Org. Lett. 2002, 4, 3887.
[14] Horneff, T.; Chuprakov, S.; Chernyak, V.; Gevorgyan, V.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 14972.
[15] Connell, R.; Scavo, F.; Helquist, P.; Akermark, B. Tetrahedron Lett. 1986, 27, 5559.
[16] Selander, N.; Fokin, V. V. J. Am. Chem. Soc. 2012, 134, 2477.
[17] Chuprakov, S.; Malik, J. A.; Zibinsky, M.; Fokin, V. V. J. Am. Chem. Soc. 2011, 133, 10352.
[18] Selander, N.; Worrell, B. T.; Chuprakov, S.; Velaparthi, S.; Fokin, V. V. J. Am. Chem. Soc. 2012, 134, 14670.
[19] Chuprakov, S.; Kwok, S. W.; Fokin, V. V. J. Am. Chem. Soc. 2013, 135, 4652.
[20] Chuprakov, S.; Worrell, B. T.; Selander, N.; Rakesh, K. S.; Fokin, V. V. J. Am. Chem. Soc. 2014, 136, 195.
[21] For recent development of triazoles see: (a) Jillian, E. S.; Huw, M. L.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 6802.
(b) Jung, D. J.; Jeon, H. J.; Kim, J. H.; Kim, Y.; Lee, S. G.. Org. Lett. 2014, 16, 2208.
(c) Yadagiri, D.; Anbarasan, P. Org. Lett. 2014, 16, 2510.
(d) Shen, H.-J.; Fu, J.-K.; Gong, J.-X.; Yang, Z. Org. Lett. 2014, 16, 5588.
(e) Xing, Y.-P.; Sheng, G.-R.; Wang, J.; Lu, P.; Wang, Y.-G. Org. Lett. 2014, 16, 1244.
(f) Chattopadhyay, B.; Gevorgyan, V. Org. Lett. 2011, 13, 3746.
[22] Shi, Y.; Gulevich, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2014, 53, 14191.
[23] Brendan, T. P.; Samantha, A. G.; Huw, M. L.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 4716.
[24] Lindsay, V. N. G.; Viart, H. M. F.; Sarpong, R. J. Am. Chem. Soc., 2015, 137, 8368.
[25] Yadagiri, D.; Anbarasan, P. Chem. Sci. 2015, 6, 5847.
[26] Zhang, Y.-S.; Tang, X.-Y.; Shi, M. Chem. Commun. 2014, 50, 15971.
[27] Spangler, J. E.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 6802.
[28] Huang, J.-P.; Yang, Y.; Chen, Z.-Y. Adv. Synth. Catal. 2016, 358, 201.
[29] Yang, Y.; Zhou, M.-B.; Ouyang, X.-H.; Pi, R.; Song, R.-J.; Li, J.-H. Angew. Chem., Int. Ed. 2015, 54, 6595.
[30] (a) Tetsuji, K.; Keiichiro, F. Heterocycles 1975, 3, 931.
(b) Renfroe, B.; Harrington, C.; Proctor, P. T. Heterocyclic Compounds: Azepines, Wiley Interscience, New York, 1984.
(c) Ganellin, C. R.; Triggle, D. J. Dictionary of Pharmacological Agents, Chapman & Hall/CRC, London, 1996.
[31] Miura, T.; Yamauchi, M.; Murakami, M. Chem. Commun. 2009, 1470.
[32] Miura, T.; Hiraga, K.; Biyajima, T.; Nakamuro, T.; Murakami, M. Org. Lett. 2013, 15, 3298.
[33] Helan, V.; Gulevich, A. V.; Gevorgyan, V. Chem. Sci. 2015, 6, 1928.
[34] Chuprakov, S.; Hwang, H. W.; Gevorgyan, V. Angew. Chem., Int. Ed. 2007, 46, 4757.

基于三氮唑类化合物的金属卡宾形成反应研究进展

Advances on the Metallocarbene Formation Reactions Based on Triazole Derivatives

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 8

Recommended Articles

Metrics

Comments

[1]	Mingyang Pang, Honghong Chang, Zhang Feng, Juan Zhang. Recent Advances in Transition-Metal-Catalyzed Tandem Dearomatization of Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1271-1291.
[2]	Cheng Gong, Jian Tang, Fei Xu, Pengjie Li, Zetian Wang, Yumin Zhang, Guoxian Yu, Liang Wang. Recent Advances in Transition-Metal-Catalyzed C—H Activation of Pyridone/Isoquinolones [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 1925-1949.
[3]	Yazhou Wang, Yuhang Zhu, Lixia Xu, Rui He, Jian Zhang. Recent Advances in Geminal-Group-Directed Alkenyl C—H Functionalization [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2000-2014.
[4]	Hui Li, Liang Yin. Research Progress on Catalytic Asymmetric Synthesis of P-Chiral Compounds [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3183-3200.
[5]	Zhen Zhang, Wenxu Chang. Progress in Transition-Metal-Catalyzed Cyclization of Carbodiimides [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1835-1850.
[6]	Li Gang, Chen Ye, Xia Jibao. Progress on Transition-Metal-Catalyzed Cross-Coupling Reactions of Ammonium Salts via C-N Bond Cleavage [J]. Chin. J. Org. Chem., 2018, 38(8): 1949-1962.
[7]	Zhou Hao, Chen Zhiyuan. Recent Achievements in the Synthesis of Sulfoximine Derivatives [J]. Chin. J. Org. Chem., 2018, 38(4): 719-737.
[8]	Wang Liang, Li Zhana, Wan Kang, Qu Xinga, Hu Siqian, Wang Feng. Progress in Diazo Compounds Mediated Transition-Metal-Catalyzed C—H Alkylation [J]. Chin. J. Org. Chem., 2016, 36(5): 889-912.