Rhodium(III)-catalyzed annulation of 2-arylimidazo[1,2-a]pyridines and alkynes via direct double C–H activation

作者: Wei Wang , Jun-Long Niu , Wen-Bo Liu , Tan-Hao Shi , Xin-Qi Hao

DOI: 10.1016/J.TET.2015.08.019

关键词:

摘要: Abstract A series of naphtho[1′,2′:4,5]imidazo[1,2- a ]pyridines were synthesized smoothly from 2-arylimidazo[1,2- and alkynes involving rhodium(III)-catalyzed C–H bond functionalization. The process selected Co(OAc) 2 ·4H O as the co-catalyst for first time minimized reaction to 2 h under air atmosphere. Some products exhibited deep blue luminescence properties.

参考文章(89)
Clara I. Herrerías, Xiaoquan Yao, Zhiping Li, Chao-Jun Li, Reactions of C−H Bonds in Water Chemical Reviews. ,vol. 107, pp. 2546- 2562 ,(2007) , 10.1021/CR050980B
Masaki Shimizu, Koji Hirano, Tetsuya Satoh, Masahiro Miura, Waste-free synthesis of condensed heterocyclic compounds by rhodium-catalyzed oxidative coupling of substituted arene or heteroarene carboxylic acids with alkynes. Journal of Organic Chemistry. ,vol. 74, pp. 3478- 3483 ,(2009) , 10.1021/JO900396Z
Avik Kumar Bagdi, Matiur Rahman, Sougata Santra, Adinath Majee, Alakananda Hajra, Copper‐Catalyzed Synthesis of Imidazo[1,2‐a]pyridines through Tandem Imine Formation‐Oxidative Cyclization under Ambient Air: One‐Step Synthesis of Zolimidine on a Gram‐Scale Advanced Synthesis & Catalysis. ,vol. 355, pp. 1741- 1747 ,(2013) , 10.1002/ADSC.201300298
Jinlei Chen, Guoyong Song, Cheng-Ling Pan, Xingwei Li, Rh(III)-catalyzed oxidative coupling of N-aryl-2-aminopyridine with alkynes and alkenes. Organic Letters. ,vol. 12, pp. 5426- 5429 ,(2010) , 10.1021/OL1022596
Souvik Rakshit, Frederic W. Patureau, Frank Glorius, Pyrrole Synthesis via Allylic sp3 C−H Activation of Enamines Followed by Intermolecular Coupling with Unactivated Alkynes Journal of the American Chemical Society. ,vol. 132, pp. 9585- 9587 ,(2010) , 10.1021/JA104305S
Denise A. Colby, Robert G. Bergman, Jonathan A. Ellman, Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation Chemical Reviews. ,vol. 110, pp. 624- 655 ,(2010) , 10.1021/CR900005N
Masaki Shimizu, Hayato Tsurugi, Tetsuya Satoh, Masahiro Miura, Rhodium-catalyzed oxidative coupling between salicylaldehydes and internal alkynes with C-H bond cleavage to produce 2,3-disubstituted chromones. Chemistry-an Asian Journal. ,vol. 3, pp. 881- 886 ,(2008) , 10.1002/ASIA.200800037
Ji-Rong Huang, Lin Dong, Bo Han, Cheng Peng, Ying-Chun Chen, Synthesis of Aza‐Fused Polycyclic Quinolines via Double CH Bond Activation Chemistry: A European Journal. ,vol. 18, pp. 8896- 8900 ,(2012) , 10.1002/CHEM.201201207
Nicolas Guimond, Serge I. Gorelsky, Keith Fagnou, Rhodium(III)-catalyzed heterocycle synthesis using an internal oxidant: improved reactivity and mechanistic studies. Journal of the American Chemical Society. ,vol. 133, pp. 6449- 6457 ,(2011) , 10.1021/JA201143V