Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2007(2): 215-218
DOI: 10.1055/s-2006-958942
DOI: 10.1055/s-2006-958942
PAPER
© Georg Thieme Verlag Stuttgart · New YorkNiobium Fluoride (NbF5): A Highly Efficient Catalyst for Solvent-Free Cyanosilylation of Aldehydes
Further Information
Received
11 September 2006
Publication Date:
14 December 2006 (online)
Publication History
Publication Date:
14 December 2006 (online)
Abstract
An efficient method for the addition of trimethylsilylcyanide (TMSCN) to aldehydes using dispersed NbF5 as the catalyst is described. Cyano transfer from TMSCN to aldehydes occurs within 10 minutes at room temperature in the presence of 0.5 mol% of NbF5 under solvent-free conditions giving cyanohydrins in excellent yields of over 95%. These conditions are extremely mild, simple and tolerate various functional groups.
Key words
aldehydes - catalysis - green chemistry - cyanohydrins - solvent-free
- 2a
North M. Synlett 1993, 807 - 2b
Effenberger F. Angew. Chem., Int. Ed. Engl. 1994, 33: 1555 - 2c
Gregory RJH. Chem. Rev. 1999, 99: 3649 - 2d
Kobayashi S.Ishitani H. Chem. Rev. 1999, 99: 1069 - 2e
Gröger H. Chem. Rev. 2003, 103: 2795 - For achiral catalysts, see:
- 3a
Matsubara S.Takai T.Utimoto K. Chem. Lett. 1991, 1447 - 3b
Whitesell JK.Apodaca R. Tetrahedron Lett. 1996, 37: 2525 - 3c
Yang Y.Wang D. Synlett 1997, 1379 - 3d
Saravanan P.Anand RV.Singh VK. Tetrahedron Lett. 1998, 39: 3823 - 3e
Bandini M.Cozzi PG.Melchiorre P.Umani-Ronchi A. Tetrahedron Lett. 2001, 42: 3041 - 3f
Bandini M.Cozzi PG.Garelli A.Melchiorre P.Umani-Ronchi A. Eur. J. Org. Chem. 2002, 3243 - 3g
Cordoba R.Plumet J. Tetrahedron Lett. 2003, 44: 6157 - 3h
Baleizão C.Gigante B.Garcia H.Corma A. Tetrahedron Lett. 2003, 44: 6813 - 3i
He B.Li Y.Feng X.Zhang G. Synlett 2004, 1776 - 3j
Iwanami K.Oriyama T. Chem. Lett. 2004, 33: 1324 - 3k
Itazaki M.Nakazawa H. Chem. Lett. 2005, 34: 1054 - 3l
Iwanami K.Aoyagi M.Oriyama T. Tetrahedron Lett. 2006, 47: 4741 - 3m
Wada M.Takahashi T.Domae T.Fukuma T.Miyoshi N.Smith K. Tetrahedron: Asymmetry 1997, 8: 3939 - 3n
Azizi N.Saidi MRJ. Organomet. Chem. 2003, 688: 283 - For chiral catalysts, see:
- 4a
Kobayashi S.Tsuchiya Y.Mukaiyama T. Chem. Lett. 1991, 541 - 4b
Ohno H.Nitta H.Tanaka K.Mori A.Inoue S. J. Org. Chem. 1992, 57: 6778 - 4c
Hayashi M.Inoue T.Miyamoto Y.Oguni N. Tetrahedron 1994, 50: 4385 - 4d
Bolm C.Müller P. Tetrahedron Lett. 1995, 36: 1625 - 4e
Holmes IP.Kagan HB. Tetrahedron Lett. 2000, 41: 7457 - 4f
Lundgren S.Lutsenko S.Jönsson C.Moberg C. Org. Lett. 2003, 5: 3663 - 4g
Li Y.He B.Qin B.Feng X.Zhang G. J. Org. Chem. 2004, 69: 7910 - 4h
Liu Y.Liu X.Xin J.Feng X. Synlett 2006, 1085 - 4i
Belokon’ YN.North M.Parsons T. Org. Lett. 2000, 2: 1617 - 4j
Kanai M.Kato N.Ichikawa E.Shibasaki M. Synlett 2005, 1491 - 4k
Chen F.-X.Feng X. Synlett 2005, 892 - 5
Brunel JM.Holmes IP. Angew. Chem. Int. Ed. 2004, 43: 2752 - 6a
Komatsu N.Uda M.Suzuki H.Takahashi T.Domae T.Wada M. Tetrahedron Lett. 1997, 38: 7215 - 6b
Loh T.-P.Xu K.-C.Ho DS.-C.Sim K.-Y. Synlett 1998, 369 - 6c
Vougioukas AE.Kagan HB. Tetrahedron Lett. 1987, 28: 5513 - 6d
Reetz MT.Drewes MW.Harms K.Reif W. Tetrahedron Lett. 1988, 29: 3295 - 6e
Evans DA.Truesdale LK.Carroll GL. J. Chem. Soc., Chem. Commun. 1973, 55 - 7
Kurono N.Yamaguchi M.Suzuki K.Ohkuma T. J. Org. Chem. 2005, 70: 6530 - 8
Fetterly BM.Verkade JG. Tetrahedron Lett. 2005, 46: 8061 - 9
Wang L.Huang X.Jiang J.Liu X.Feng X. Tetrahedron Lett. 2006, 47: 1581 - 10
Song JJ.Gallou F.Reeves JT.Tan Z.Yee NK.Senanayake CH. J. Org. Chem. 2006, 71: 1273 - 11
Suzuki Y.Abu Bakar MD.Muramatsu K.Sato M. Tetrahedron 2006, 62: 4227 - 12a
North M. Tetrahedron: Asymmetry 2003, 14: 147 - 12b
Belokon YN.Ishibashi E.Nomura H.North M. Chem. Commun. 2006, 1775 - 12c
Hamashima Y.Sawada D.Kanai M.Shibasaki M. J. Am. Chem. Soc. 1999, 121: 2641 - 12d
Hamashima Y.Sawada D.Nogami H.Kanai M.Shibasaki M. Tetrahedron 2001, 57: 805 - 12e
Casas J.Najera C.Sansano JM.Saa JM. Org. Lett. 2002, 4: 2589 - 12f
Furest DE.Jacobsen EN. J. Am. Chem. Soc. 2005, 127: 8964 - 12g Special symposium for the synthesis of non-racemic cyanohydrins, see: Tetrahedron 2004, 60: 10371
- 13a
Kim SS.Song DH. Eur. J. Org. Chem. 2005, 1777 - 13b
Kim SS.Kwak JM. Tetrahedron 2006, 62: 49 - 13c
Kim SS.Lee SH.Kwak JM. Tetrahedron: Asymmetry 2006, 17: 1165 - 13d
Kim SS.Lee SH. Synth. Commun. 2005, 35: 751 - 13e
Kim SS. Pure. Appl. Chem. 2006, 78: 977 - 14a
Kim SS.Rajagopal G.Song DH. J. Organomet. Chem. 2004, 689: 1734 - 14b
Kim SS.Kim DW.Rajagopal G. Synthesis 2004, 213 - 14c
Kim SS.Rajagopal G.Kim DW.Song DH. Synth. Commun. 2004, 34: 2973 - 15a
Clark JH. Catalysis of Organic Reactions using Supported Inorganic Reagents VCH; New York: 1994.Reference Ris Wihthout Link - 15b
Chemistry of Waste Minimization
Clark JH. Chapman and Hall; London: 1995.Reference Ris Wihthout Link - 16a
Howrath J.Gillespie K. Tetrahedron Lett. 1996, 37: 6011 - 16b
Andrade CKZ.Azevedo NR. Tetrahedron Lett. 2001, 42: 6473 - 16c
Arai S.Sudo Y.Nishida A. Synlett 2004, 1104 - 17
Karmi B.MaMani L. Org. Lett. 2004, 6: 4813 - 18
Kantham ML.Sreekanth P.Shanthi PL. Green Chem. 2000, 2: 47
References
Dr. G. Rajagopal is a Brain Pool Scientist from the Department of Chemistry, BSA Crescent Engineering College, Chennai 600 048, India. He was assisted by a grant from the Korean Federation of Science and Technology Societies and Korea Science and Engineering Foundation.