Remote alkylation of N-(quinolin-8-yl)benzamides with alkyl bromides via ruthenium(II)-catalyzed C–H bond activation

作者: Arumugam Mariappan , Krishna Mohan Das , Masilamani Jeganmohan

DOI: 10.1039/C8OB00581H

关键词:

摘要: A ruthenium(II) catalyzed remote C-5 alkylation of the quinoline ring N-(quinolin-8-yl)benzamides with alkyl bromides via C–H bond activation is described. Various substituted reacted tertiary or secondary primary giving alkylated products in good to moderate yields. Herein, ruthenium effected aromatic as a key step. It has been proved by deuterium labelling studies and mechanistic investigations.

参考文章(81)
Xuefeng Cong, Xiaoming Zeng, Iron-Catalyzed, Chelation-Induced Remote C–H Allylation of Quinolines via 8-Amido Assistance Organic Letters. ,vol. 16, pp. 3716- 3719 ,(2014) , 10.1021/OL501534Z
Huijie Qiao, Suyan Sun, Fan Yang, Yu Zhu, Weiguo Zhu, Yaxi Dong, Yusheng Wu, Xiangtao Kong, Ling Jiang, Yangjie Wu, Copper(I)-Catalyzed Sulfonylation of 8-Aminoquinoline Amides with Sulfonyl Chlorides in Air Organic Letters. ,vol. 17, pp. 6086- 6089 ,(2015) , 10.1021/ACS.ORGLETT.5B03114
Zhe Dong, Jianchun Wang, Guangbin Dong, Simple Amine-Directed Meta-Selective C–H Arylation via Pd/Norbornene Catalysis Journal of the American Chemical Society. ,vol. 137, pp. 5887- 5890 ,(2015) , 10.1021/JACS.5B02809
M. Ramu Yadav, Raja K. Rit, Majji Shankar, Akhila K. Sahoo, Sulfoximine-Directed Ruthenium-Catalyzed ortho-C–H Alkenylation of (Hetero)Arenes: Synthesis of EP3 Receptor Antagonist Analogue Journal of Organic Chemistry. ,vol. 79, pp. 6123- 6134 ,(2014) , 10.1021/JO5008465
Christopher J. Whiteoak, Oriol Planas, Anna Company, Xavi Ribas, A first example of cobalt-catalyzed remote C-H functionalization of 8-aminoquinolines operating through a single electron transfer mechanism Advanced Synthesis & Catalysis. ,vol. 358, pp. 1679- 1688 ,(2016) , 10.1002/ADSC.201600161
Zhoulong Fan, Jiabin Ni, Ao Zhang, Meta-Selective CAr-H Nitration of Arenes through a Ru3(CO)12-Catalyzed Ortho-Metalation Strategy. Journal of the American Chemical Society. ,vol. 138, pp. 8470- 8475 ,(2016) , 10.1021/JACS.6B03402
Anup Mandal, Harekrishna Sahoo, Mahiuddin Baidya, Copper-Catalyzed 8-Aminoquinoline-Directed Selenylation of Arene and Heteroarene C–H Bonds Organic Letters. ,vol. 18, pp. 3202- 3205 ,(2016) , 10.1021/ACS.ORGLETT.6B01420
Ramasamy Manoharan, Ganesan Sivakumar, Masilamani Jeganmohan, Cobalt-catalyzed C-H olefination of aromatics with unactivated alkenes. Chemical Communications. ,vol. 52, pp. 10533- 10536 ,(2016) , 10.1039/C6CC04835H
Hao Chen, Pinhua Li, Min Wang, Lei Wang, Nickel-Catalyzed Site-Selective C–H Bond Difluoroalkylation of 8-Aminoquinolines on the C5-Position Organic Letters. ,vol. 18, pp. 4794- 4797 ,(2016) , 10.1021/ACS.ORGLETT.6B02166