Facile synthesis of 2-alkenylazaarenes via dehydrative coupling of 2-methylazaarenes with aldehydes ‘on water’

[Display omitted] •Synthesis of 2-alkenylazaarenes via reaction of 2-methylazaarenes with aldehydes.•The aliphatic aldehyde problem was harnessed using water as a solvent.•Water as solvent and no catalyst render this method atom-economic and green. A catalyst-free dehydrative coupling of 2-methylaza...

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Bibliographic Details
Published in:Tetrahedron letters 2016-10, Vol.57 (41), p.4533-4536
Main Authors: Fu, Shiheng, Wang, Liang, Dong, Haoxun, Yu, Junqiang, Xu, Lubin, Xiao, Jian
Format: Article
Language:English
Subjects:
2-Alkenylazaarene
2-Methylazaarene
C(sp3)–H functionalization
Olefination
On water
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Summary:[Display omitted] •Synthesis of 2-alkenylazaarenes via reaction of 2-methylazaarenes with aldehydes.•The aliphatic aldehyde problem was harnessed using water as a solvent.•Water as solvent and no catalyst render this method atom-economic and green. A catalyst-free dehydrative coupling of 2-methylazaarenes with aldehydes ‘on water’ has been developed for efficient synthesis of (E)-2-alkenylazaarenes. The challenging addition/dehydration of aliphatic aldehyde was successfully implemented using water as a solvent. A variety of 2-methylazaarenes, aromatic and aliphatic aldehydes were well tolerated.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.08.065