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Assembly of Conjugated Enynes and Substituted Indoles via CuI/Amino Acid-Catalyzed Coupling of 1-Alkynes with Vinyl Iodides and 2-Bromotrifluoroacetanilides

Feng Liu and Dawei Ma*

*State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China, Email: madwmail.sioc.ac.cn

F. Liu, D. Ma, J. Org. Chem., 2007, 72, 4844-4850.

DOI: 10.1021/jo070547x (free Supporting Information)


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Abstract

Cross-coupling of 1-alkynes with vinyl iodides catalyzed by CuI/N,N-dimethylglycine affords conjugated enynes in good to excellent yields. Heating a mixture of 2-bromotrifluoroacetanilide, 1-alkyne in the presence of CuI/L-proline leads to the formation of the corresponding indole.

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Facile Access to Polysubstituted Indoles via a Cascade Cu-Catalyzed Arylation-Condensation Process

Y. Chen, X. Xie, D. Ma, J. Org. Chem., 2007, 72, 9329-9334.


Key Words

Enynes, Indoles


ID: J42-Y2007-2050