Concise Report
Palladium-Catalyzed Tandem Cyclization Strategy for the Assembly of 3-Halo-1,2,5-triarylpyrroles from N-Alkylanilines and Haloalkynes
Songjia Fang,
Huanfeng Jiang,
Wanqing Wu,
Songjia Fang
Key Laboratory of Functional Molecular Engineering of Guangdong Province, State Key Laboratory of Luminescent Materials and Devices, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong, 510640 China
Search for more papers by this authorHuanfeng Jiang
Key Laboratory of Functional Molecular Engineering of Guangdong Province, State Key Laboratory of Luminescent Materials and Devices, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong, 510640 China
Search for more papers by this authorCorresponding Author
Wanqing Wu
Key Laboratory of Functional Molecular Engineering of Guangdong Province, State Key Laboratory of Luminescent Materials and Devices, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong, 510640 China
E-mail: [email protected]Search for more papers by this authorSongjia Fang,
Huanfeng Jiang,
Wanqing Wu,
Songjia Fang
Key Laboratory of Functional Molecular Engineering of Guangdong Province, State Key Laboratory of Luminescent Materials and Devices, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong, 510640 China
Search for more papers by this authorHuanfeng Jiang
Key Laboratory of Functional Molecular Engineering of Guangdong Province, State Key Laboratory of Luminescent Materials and Devices, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong, 510640 China
Search for more papers by this authorCorresponding Author
Wanqing Wu
Key Laboratory of Functional Molecular Engineering of Guangdong Province, State Key Laboratory of Luminescent Materials and Devices, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong, 510640 China
E-mail: [email protected]Search for more papers by this authorComprehensive Summary
This report discloses a distinctive palladium-catalyzed sequential tandem cyclization reaction of two molecular haloalkynes and one molecular N-alkylanilines, leading to the efficient assembly of various 3-halo-1,2,5-triarylpyrrole derivatives. Two carbon-carbon triple bonds and one carbon-halogen bond in two molecular haloalkynes are transformed conveniently in one single step, which may involve the aminoalkynylation of haloalkyne and cyclization of the newly formed enyne intermediate. The high chemo- and regioselectivities, good functional group tolerance and late-stage modification of the halopyrrole products further illustrate the synthetic value of this strategy.
Supporting Information
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Appendix S1: Supporting Information |
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