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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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References

  1. M. Breuer, K. Ditrich, T. Habicher, B. Hauer, M. Kesseler, R. Stürmer, T. Zelinski, Angew. Chem. Int. Ed. 43, 788 (2004)

    Article  CAS  Google Scholar 

  2. P.I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 43, 5138 (2004)

    Article  CAS  Google Scholar 

  3. M. Rueping. J. Dufour, F. R. Schoepke, Green Chemistry 13 1084 (2011)

  4. A. Chan, K.A. Scheidt, Org. Lett. 7, 905 (2005)

    Article  CAS  Google Scholar 

  5. V. Nair, S. Vellalath, B.P. Babu, Chem. Soc. Rev. 37, 2691 (2008)

    Article  CAS  Google Scholar 

  6. D. Enders, T. Balensiefer, Acc. Chem. Res. 37, 534 (2004)

    Article  CAS  Google Scholar 

  7. X. Bugaut, F. Glorius, Chem. Soc. Rev. 41, 3511 (2012)

    Article  CAS  Google Scholar 

  8. J.S. Johnson, Angew. Chem. Int. Ed. 43, 1326 (2004)

    Article  CAS  Google Scholar 

  9. D. Enders, U. Kallfass, Angew. Chem. Int. Ed. 41, 1743 (2002)

    Article  CAS  Google Scholar 

  10. J.R. de Alaniz, M.S. Kerr, J.L. Moore, T. Rovis, J. Org. Chem. 73, 2033 (2008)

    Article  Google Scholar 

  11. P. V. G. Reddy, S. Tabassum, A. Blanrue, R. Wilhelm, Chem. Commun. 5910 (2009)

  12. A. Chan, K.A. Scheidt, J. Am. Chem. Soc. 129, 5334 (2007)

    Article  CAS  Google Scholar 

  13. Y.-K. Liu, R. Li, L. Yue, B.-J. Li, Y.-C. Chen, Y. Wu, L.-S. Ding, Org. Lett. 8, 1521 (2006)

    Article  Google Scholar 

  14. L. He, Y.-R. Zhang, X.-L. Huang, S. Ye, Synthesis 2008, 2825 (2008)

    Article  Google Scholar 

  15. J.J. Song, F. Gallou, J.T. Reeves, Z. Tan, N.K. Yee, C.H. Senanayake, J. Org. Chem. 71, 1273 (2006)

    Article  CAS  Google Scholar 

  16. G.A. Grasa, T. Güveli, R. Singh, S.P. Nolan, J. Org. Chem. 68, 2812 (2003)

    Article  CAS  Google Scholar 

  17. E.F. Connor, G.W. Nyce, M. Myers, A. Möck, J.L. Hedrick, J. Am. Chem. Soc. 124, 914 (2002)

    Article  CAS  Google Scholar 

  18. K. Nicolaou, D.W. Kim, R. Baati, Angew. Chem. Int. Ed. 41, 3701 (2002)

    Article  CAS  Google Scholar 

  19. F.-X. Felpin, J. Lebreton, J. Org. Chem. 67, 9192 (2002)

    Article  CAS  Google Scholar 

  20. A. Massa, M.R. Acocella, V.D. Sio, R. Villano, A. Scettri, Tetrahedron Asymmetry 20, 202 (2009)

    Article  CAS  Google Scholar 

  21. S. Kobayashi, K. Nishio, Tetrahedron Lett. 34, 3453 (1993)

    Article  CAS  Google Scholar 

  22. S. Kobayashi, C. Ogawa, H. Konishi, M. Sugiura, J. Am. Chem. Soc. 125, 6610 (2003)

    Article  CAS  Google Scholar 

  23. Y.S. Oh, S. Kotani, M. Sugiura, M. Nakajima, Tetrahedron Asymmetry 21, 1833 (2010)

    Article  CAS  Google Scholar 

  24. I. Chataigner, U. Piarulli, C. Gennari, Tetrahedron Lett. 40, 3633 (1999)

    Article  CAS  Google Scholar 

  25. E. Scott, X. Su, Y. Nishigaichi, D.M. Coe, K.-T. Wong, S.B. Winter, J.Y. Choi, J. Org. Chem. 64, 1958 (1999)

    Article  Google Scholar 

  26. P. Renaud, N. Moufid, L.H. Kuo, D.P. Curran, J. Org. Chem. 59, 3547 (1994)

    Article  CAS  Google Scholar 

  27. K. Iseki, S. Mizuno, Y. Kuroki, Y. Kobayashi, Tetrahedron 55, 977 (1999)

    Article  CAS  Google Scholar 

  28. K. Ishimaru, K. Ono, Y. Tanimura, T. Kojima, Synth. Commun. 41, 3627 (2011)

    Article  CAS  Google Scholar 

  29. W.-L. Wong, C.-S. Lee, H.-K. Leung, H.-L. Kwong, Org. Biomol. Chem. 2, 1967 (2004)

    Article  CAS  Google Scholar 

  30. J.F. Traverse, Y. Zhao, A.H. Hoveyda, L. Marc, Org. Lett. 7, 3151 (2005)

    Article  CAS  Google Scholar 

  31. J. R. Fulton. J. E. Glover. L. Kamara, G. J. Rowlands, Chem. Commun. 47 433 (2011)

  32. S. Kotani, S. Hashimoto, M. Nakajima, Tetrahedron 63, 3122 (2007)

    Article  CAS  Google Scholar 

  33. M. Nakajima, S. Kotani, T. Ishizuka, S. Hashimoto, Tetrahedron Lett. 46, 157 (2005)

    Article  CAS  Google Scholar 

  34. W.C. Still, M. Kahn, A. Mitra, J. Org. Chem. 43, 2923 (1978)

    Article  CAS  Google Scholar 

  35. S. Tabassum, M.A. Gilani, R. Wilhelm, Tetrahedron Asymmetry 22, 1632 (2011)

    Article  CAS  Google Scholar 

  36. M. J. Frisch. G. W. Trucks. H. B. Schlegel. G. E. Scuseria. M. A. Robb. J. R. Cheeseman. G. Scalmani. V. Barone. B. Mennucci. G. A. Petersson. H. Nakatsuji. M. Caricato. X. H. P. H. Li. A. F. I. J. Bloino. G. Zheng. J. L. Sonnenberg. M. Hada. M. Ehara. K. Toyota. R. Fukuda. Hasegawa. M. Ishida. T. Nakajima. Y. Honda. O. Kitao. H. Nakai. T. Vreven. J. A. Montgomery. J. E. P. Jr.. F. O. M. Bearpark. J. J. H. E. Brothers. K. N. Kudin. V. N. Staroverov. R. Kobayashi. J. Normand. K. Raghavachari. A. Rendell. J. C. Burant. S. S. Iyengar. J. T. M. Cossi. N. Rega. J. M. Millam. M. Klene. J. E. Knox. J. B. Cross. V. Bakken. C. Adamo. J. Jaramillo. R. Gomperts. R. E. Stratmann. O. Yazyev. A. J. Austin. R. Cammi. C. Pomelli. J. W. Ochterski. R. L. Martin. K. Morokuma. V. G. Zakrzewski. G. A. Voth. P. Salvador. J. J. Dannenberg. S. Dapprich. A. D. Daniels. Ö. Farkas. J. B. Foresman. J. V. Ortiz. J. Cioslowski, D. J. Fox, Gaussian, Inc., 09, Revision A.1, Wallingford CT, (2009)

  37. A.D. Becke, Phys. Rev. A 38, 3098 (1988)

    Article  CAS  Google Scholar 

  38. MarvinView 5.9.4. ChemAxon. (2012)

  39. J. Foresman, E. Frish, Gaussian Inc (Pittsburg, USA, 1996)

    Google Scholar 

  40. A.E. Reed, L. Curtiss, A.F. Weinhold, Chem. Rev. 88, 899 (1988)

    Article  CAS  Google Scholar 

  41. Y. Génisson, ML-d Viguerie, C. André, M. Baltas, L. Gorrichon, Tetrahedron Asymmetry 16, 1017 (2005)

    Article  Google Scholar 

  42. B. Çetinkaya, S. Demir, I. Özdemir, L. Toupet, D. Sémeril, P. Bruneau, H. Dixneuf, New J. Chem. 25, 519 (2001)

    Article  Google Scholar 

  43. F. Demirhan, Ö. Yıldırım, B. Çetinkaya, Transition Met. Chem. 28, 558 (2003)

    Article  CAS  Google Scholar 

  44. J. Carreras, A. Avenoza, J. Busto, J. Peregrina, J. Org. Chem. 72, 3112 (2007)

    Article  CAS  Google Scholar 

  45. J.D. Short, S. Attenoux, J. Berrisford, Tetrahedron Lett. 38, 2351 (1997)

    Article  CAS  Google Scholar 

  46. O. Sereda. S. Tabassum, R. Wilhelm, Asymmetric Organocatalysis 349 (2009)

  47. A.D. Dilman, S.L. Ioffe, Chem. Rev. 103, 733 (2003)

    Article  CAS  Google Scholar 

  48. C.-G. Zhan. J. A. Nichols, D. A. Dixon, J. Phys. Chem. A 107, 4184 (2003)

  49. S. Deuri, P. Phukan, Comput. Theor. Chem. 980, 49 (2012)

    Article  CAS  Google Scholar 

  50. R.G. Parr, Lv Szentpály, S. Liu, J. Am. Chem. Soc. 121, 1922 (1999)

    Article  CAS  Google Scholar 

  51. P. K. Chattaraj. S. Giri, S. Duley, Chemical Reviews 111 PR43 (2011)

  52. W. Yang, W.J. Mortier, J. Am. Chem. Soc. 108, 5708 (1986)

    Article  CAS  Google Scholar 

  53. R.K. Roy, J. Phys. Chem. A 108, 4934 (2004)

    Article  CAS  Google Scholar 

  54. R.K. Roy, V. Usha, B.K. Patel, K. Hirao, J. Comput. Chem. 27, 773 (2006)

    Article  CAS  Google Scholar 

  55. R. K. Roy. P. Bagaria. S. Naik. V. Kavala, B. K. Patel, J. Phys. Chem. A 110 2181 (2006)

  56. P. K. Chattaraj. B. Maiti, U. Sarkar, J. Phys. Chem. A 107 4973 (2003)

  57. D. Roy. R. Parthasarathi. J. Padmanabhan. U. Sarkar. V. Subramanian, P. Chattaraj, J. Phys. Chem. A 110 1084 (2006)

  58. P. Pérez, L.R. Domingo, M. Duque-Noreña, E. Chamorro, J. Mol. Struct. Theochem. 895, 86 (2009)

    Article  Google Scholar 

  59. C. Lee, W. Yang, R.G. Parr, J. Mol. Struct. Theochem. 163, 305 (1988)

    Article  Google Scholar 

  60. A. Cedillo, R. Contreras, J. Mex. Chem. Soc. 56, 257 (2012)

    CAS  Google Scholar 

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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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