Synthesis of trifluoroalkyl or difluoroalkyl phenanthridine derivatives via cascade reaction using an intramolecular cyano group as a radical acceptor under photoredox catalysis

作者: Xu Liu , Zhongjie Wu , Zeguo Zhang , Ping Liu , Peipei Sun

DOI: 10.1039/C7OB02804K

关键词:

摘要: In the presence of Ru(phen)3Cl2 or fac-Ir(ppy)3 under visible-light irradiation, addition fluorinated radicals to N-arylacrylamides followed by an intramolecular cyano group insertion cascade cyclization process produced trifluoroalkyl difluoroalkyl phenanthridine derivatives in moderate good yields. Three easily available fluoroalkylated reagents CF3SO2Cl, BrCF2CO2Et and BrCF2PO(OEt)2 were used as sources radicals.

参考文章(77)
David A. Nagib, Mark E. Scott, David W. C. MacMillan, Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis Journal of the American Chemical Society. ,vol. 131, pp. 10875- 10877 ,(2009) , 10.1021/JA9053338
Chunghyeon Yu, Naeem Iqbal, Sehyun Park, Eun Jin Cho, Selective difluoroalkylation of alkenes by using visible light photoredox catalysis. Chemical Communications. ,vol. 50, pp. 12884- 12887 ,(2014) , 10.1039/C4CC05467A
Qing-Yun Chen, Sheng-Wen Wu, Methyl fluorosulphonyldifluoroacetate; a new trifluoromethylating agent Journal of The Chemical Society, Chemical Communications. pp. 705- 706 ,(1989) , 10.1039/C39890000705
Takeshi Nakanishi, Masanobu Suzuki, Revision of the structure of fagaridine based on the comparison of UV and NMR data of synthetic compounds. Journal of Natural Products. ,vol. 61, pp. 1263- 1267 ,(1998) , 10.1021/NP980193S
Xiao-Hui Cao, Xiangqiang Pan, Peng-Jun Zhou, Jian-Ping Zou, Olayinka Taiwo Asekun, Manganese(III)-mediated direct Csp2–H radical trifluoromethylation of coumarins with sodium trifluoromethanesulfinate Chemical Communications. ,vol. 50, pp. 3359- 3362 ,(2014) , 10.1039/C3CC49689A
Bin Yang, Xiu-Hua Xu, Feng-Ling Qing, Copper-mediated radical 1,2-bis(trifluoromethylation) of alkenes with sodium trifluoromethanesulfinate. Organic Letters. ,vol. 17, pp. 1906- 1909 ,(2015) , 10.1021/ACS.ORGLETT.5B00601
Yingda Ye, Melanie S. Sanford, Merging Visible-Light Photocatalysis and Transition-Metal Catalysis in the Copper-Catalyzed Trifluoromethylation of Boronic Acids with CF3I Journal of the American Chemical Society. ,vol. 134, pp. 9034- 9037 ,(2012) , 10.1021/JA301553C