A Three-Component Reaction by Photoinduced Electron Transfer Mechanism with N-Protected Pyrroles as Neutral Carbon Nucleophiles
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- 作者：Jian Tang ; Jia-Jun Yue ; Fei-Fei Tao ; Guenter Grampp ; Bing-Xiang Wang ; Fang Li ; Xue-Zheng Liang ; Yong-Miao Shen ; Jian-Hua Xu
- 刊名：Journal of Organic Chemistry
- 出版年：2014
- 出版时间：August 15, 2014
- 年：2014
- 卷：79
- 期：16
- 页码：7572-7582
- 全文大小：449K
- ISSN：1520-6904
文摘
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鈥揅 bonds between the three reactants.