文献类型：期刊文献

英文题名：A Three-Component Reaction by Photoinduced Electron Transfer Mechanism with N-Protected Pyrroles as Neutral Carbon Nucleophiles

作者：Tang, Jian[1,2];Yue, Jia-Jun[3];Tao, Fei-Fei[1];Grampp, Guenter[4];Wang, Bing-Xiang[2];Li, Fang[1];Liang, Xue-Zheng[1];Shen, Yong-Miao[1];Xu, Jian-Hua[3]

机构：[1]Shaoxing Univ, Sch Chem & Chem Engn, Shaoxing 312000, Peoples R China;[2]Nanjing Normal Univ, Sch Chem & Mat Sci, Jiangsu Key Lab Biofunct Mat, Nanjing 210097, Jiangsu, Peoples R China;[3]Nanjing Univ, Inst Chem & Chem Engn, Nanjing 210093, Jiangsu, Peoples R China;[4]Graz Univ Technol, A-8010 Graz, Austria

年份：2014

卷号：79

期号：16

起止页码：7572

外文期刊名：JOURNAL OF ORGANIC CHEMISTRY

收录：SCI-EXPANDED(收录号：WOS:000340517600031)、、EI(收录号：20143418092856)、Scopus(收录号：2-s2.0-84906084928)、WOS、CCR-EXPANDED(收录号：WOS:000340517600031)

基金：This work was supported by the National Natural Science Foundation of China (NSFC 21202101 and 51372154) and Zhejiang Provincial Natural Science Foundation (Y4080395 and LY12B01007).

语种：英文

外文关键词：Aromatic compounds - Carbon - Nucleophiles - Olefins

外文摘要：A new photoinduced three-component reaction between a cyanoarene, an alkene and an N-protected pyrrole has been developed. This reaction extended the scope of the photo-NOCAS reaction by introducing pyrrole as a neutral carbon-centered nucleophile. The cyanoarenes used include tetracyanobenzene (TCB), 2,3,5,6-tetrafluoro-1,4-dicyanobenzene (TFDCB) and 1,4-dicyanobenzene (DCB). N-Methyl, N-phenyl and N-Boc pyrroles are suitable nucleophiles in the reaction. Taking advantage of the strong electron acceptor ability of the singlet excited TCB, a wide range of alkenes, including the highly electron deficient 4-fluoro-, 4-chloro-, 2,3,4,5,6-pentafluorostyrenes and N-methylmaleimide take part in this reaction, leading to the simultaneous 1,2-diarylation of the alkene and the regioselective 2-alkylation of the pyrrole ring via sequential formation of two new C-C bonds between the three reactants.