Copper-mediated C3-cyanation of indoles by the combination of amine and ammonium

A copper-promoted C3-cyanation of both the free N-H and N-protected indoles by N,N,N',N'-tetramethyl-ethane-1,2-diamine (TMEDA) and ammonium is achieved. The iminium ion acts as the intermediate in this transformation, which is sequentially electrophilically attacked by indole and H2O foll...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2014-01, Vol.50 (18), p.2315-2317
Main Authors: Liu, Bin, Wang, Jiehui, Zhang, Bo, Sun, Yang, Wang, Lei, Chen, Jianbin, Cheng, Jiang
Format: Article
Language:English
Subjects:
Aldehydes
Amines
Amines - chemistry
Ammonium Compounds - chemistry
Chemical attack
Copper - chemistry
Efficiency
Indoles
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Nitriles
Nitriles - chemical synthesis
Nitriles - chemistry
Tolerances
Transformations
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Summary:A copper-promoted C3-cyanation of both the free N-H and N-protected indoles by N,N,N',N'-tetramethyl-ethane-1,2-diamine (TMEDA) and ammonium is achieved. The iminium ion acts as the intermediate in this transformation, which is sequentially electrophilically attacked by indole and H2O followed by hydrolyzation to form the aldehyde. Then the reaction between the aldehyde and ammonium afforded nitriles. The reaction employs O2 as a clean oxidant with good efficiency and functional group tolerance. Thus, it represents a facile and safe procedure leading to 3-cyano indoles.
ISSN:1359-7345
1364-548X
DOI:10.1039/c3cc49339c