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- Title
First examples of carbene-catalyzed allylation of benzaldehyde with allyltrichlorosilane.
- Authors
Tabassum, Sobia; Gilani, Mazhar; Ayub, Khurshid; Wilhelm, René
- Abstract
We report here first examples of carbene-catalyzed allylation of benzaldehyde. N-Heterocyclic carbenes applied here, 9a and 10a, were derived from imidazolinium zwitterions, and contained sulfonate and sulfamate substituents, respectively. Different reaction conditions such as temperature, organic solvents, additive and bases were used to optimize the reaction. Sulfonate substituted NHC 9a is found more efficient organocatalyst for the allyltion of benzaldehyde (greater than 99 % yield at lower temperature) than sulfamate-based NHC 10a (a yield of no more than 15 %). These results are justified on the basis of philicity descriptors of the NHCs and their corresponding allyldichlorosilane complexes. Graphical abstract: [Figure not available: see fulltext.]
- Subjects
CARBENES; BENZALDEHYDE; ALLYLATION; SILANE; SUBSTITUTION reactions
- Publication
Journal of the Iranian Chemical Society, 2015, Vol 12, Issue 7, p1199
- ISSN
1735-207X
- Publication type
Article
- DOI
10.1007/s13738-014-0582-8