Regioselective copper-catalyzed thiolation of imidazo[1,2-a]pyridines: an efficient C–H functionalization strategy for C–S bond formation

作者: Hua Cao , Longbin Chen , Jingyun Liu , Huiyin Cai , Hao Deng

DOI: 10.1039/C5RA01342A

关键词: Bond formationMolecular oxygenOrganic chemistrySurface modificationMedicinal chemistryCatalysisChemistryRegioselectivityCopperCopper catalyzed

摘要: A highly regioselective C–H/S–H cross-coupling of imidazo[1,2-a]pyridines with thiols has been developed using molecular oxygen to form the C-3 sulfenated products in presence a copper catalyst. It represents simple process for formation C–S bonds prepare thioether-decorated imidazo[1,2-a]pyridines. The reaction proceeds smoothly broad range substrates give good yields.

参考文章(59)
Wenlei Ge, Xun Zhu, Yunyang Wei, Aerobic Multicomponent Tandem Synthesis of 3‐Sulfenylimidazo[1,2‐a]pyridines from Ketones, 2‐Aminopyridines, and Disulfides European Journal of Organic Chemistry. ,vol. 2013, pp. 6015- 6020 ,(2013) , 10.1002/EJOC.201300905
An-Xi Zhou, Xue-Yuan Liu, Ke Yang, Shu-Chun Zhao, Yong-Min Liang, Copper-catalyzed direct thiolation of azoles with aliphatic thiols Organic and Biomolecular Chemistry. ,vol. 9, pp. 5456- 5462 ,(2011) , 10.1039/C1OB05395G
Ly Dieu Tran, Ilya Popov, Olafs Daugulis, Copper-Promoted Sulfenylation of sp2 C–H Bonds Journal of the American Chemical Society. ,vol. 134, pp. 18237- 18240 ,(2012) , 10.1021/JA3092278
Chao Dai, Zhaoqing Xu, Fei Huang, Zhengkun Yu, Yan-Feng Gao, Lewis Acid-Catalyzed, Copper(II)-Mediated Synthesis of Heteroaryl Thioethers under Base-Free Conditions Journal of Organic Chemistry. ,vol. 77, pp. 4414- 4419 ,(2012) , 10.1021/JO202624S
R. Boston, K. Awaya, T. Nakayama, W. Ogasawara, S. R. Hall, Formation of superconducting yttrium barium copper oxide using sulphur-containing templates RSC Advances. ,vol. 4, pp. 26824- 26828 ,(2014) , 10.1039/C4RA04745A
Zhen Li, Jianquan Hong, Xigeng Zhou, An efficient and clean CuI-catalyzed chalcogenylation of aromatic azaheterocycles with dichalcogenides Tetrahedron. ,vol. 67, pp. 3690- 3697 ,(2011) , 10.1016/J.TET.2011.03.067
Simon Feldbæk Nielsen, Elsebet Østergaard Nielsen, Gunnar M. Olsen, Tommy Liljefors, Dan Peters, Novel potent ligands for the central nicotinic acetylcholine receptor: synthesis, receptor binding, and 3D-QSAR analysis. Journal of Medicinal Chemistry. ,vol. 43, pp. 2217- 2226 ,(2000) , 10.1021/JM990973D
Poulomi Majumdar, Anita Pati, Manabendra Patra, Rajani Kanta Behera, Ajaya Kumar Behera, Acid hydrazides, potent reagents for synthesis of oxygen-, nitrogen-, and/or sulfur-containing heterocyclic rings. Chemical Reviews. ,vol. 114, pp. 2942- 2977 ,(2014) , 10.1021/CR300122T
Xiaoyun Zhang, Weilan Zeng, Yuan Yang, Hui Huang, Yun Liang, Copper-Catalyzed Double C–S Bonds Formation via Different Paths: Synthesis of Benzothiazoles from N-Benzyl-2-iodoaniline and Potassium Sulfide Organic Letters. ,vol. 16, pp. 876- 879 ,(2014) , 10.1021/OL403638D