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First examples of carbene-catalyzed allylation of benzaldehyde with allyltrichlorosilane

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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.

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Acknowledgments

We acknowledge Higher Education Commission of Pakistan for the financial support.

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Authors and Affiliations

  1. Interdisciplinary Research Center in Biomedical Materials, COMSATS Institute of Information Technology, Defence Road, Off Raiwind Road, Lahore, Pakistan

    Sobia Tabassum

  2. Department of Chemical Engineering, COMSATS Institute of Information Technology, Defence Road, Off Raiwind Road, Lahore, Pakistan

    Mazhar Amjad Gilani

  3. Department of Chemistry, College of Science, King Faisal University, Al-Ahsa, 31982, Kingdom of Saudi Arabia

    Khurshid Ayub

  4. Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad, 22060, Pakistan

    Khurshid Ayub

  5. Department of Chemistry, University of Paderborn, Warburgerstrasse 100, 33098, Paderborn, Germany

    René Wilhelm

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  1. Sobia Tabassum
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Correspondence to Sobia Tabassum.

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Tabassum, S., Gilani, M.A., Ayub, K. et al. First examples of carbene-catalyzed allylation of benzaldehyde with allyltrichlorosilane. J IRAN CHEM SOC 12, 1199–1205 (2015). https://doi.org/10.1007/s13738-014-0582-8

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  • DOI: https://doi.org/10.1007/s13738-014-0582-8

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