Schmidt reaction in ionic liquids: Highly efficient and selective conversion of aromatic and heteroaromatic aldehydes to nitriles with [BMIM(SO3H)][OTf] as catalyst and [BMIM][PF6] as solvent

Tetrahedron Letters

Volumn 54, Issue 17, 2013, Pages 2177-2179

  Nandi, Ganesh C ^a   Laali, Kenneth K ^a  

^a UNIVERSITY OF NORTH FLORIDA   (United States)

Author keywords

BMIM(SO3H) OTf ; BMIM PF6 ; Aromatic aldehydes; Nitriles; Schmidt reaction

Indexed keywords

ALDEHYDE; IONIC LIQUID; LEWIS ACID; NITRILE; SOLVENT;

ARTICLE; BIOTRANSFORMATION; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOLATION AND PURIFICATION; QUANTITATIVE ANALYSIS; SCHMIDT REACTION;

EID: 84875242509     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.02.051     Document Type: Article

References (21)

1. R.G. Kalkhambkar, S.D. Bunge, and K.K. Laali Tetrahedron Lett. 52 2011 5184 5187 and references cited therein
2. A. Hassner, and I. Namboothiri Organic Syntheses Based on Name Reactions 3rd ed. 2012 Elsevier Oxford, UK p 420
3. R. Liu, O. Gutierrez, D.J. Tantillo, and J. Aubé J. Am. Chem. Soc. 134 2012 6528 6531
4. K.J. Frankowski, J.E. Golden, Y. Zeng, Y. Lei, and J. Aubé.J. Am. Chem. Soc. 130 2008 6018 6024
5. P. Chaudhry, F. Schoenen, B. Neuenswander, G.H. Lushington, and J. Aubé J. Comb. Chem. 9 2007 473 476
6. R. Iyengar, K. Schildknegt, M. Morton, and J. Aubé J. Org. Chem. 70 2005 10645 10652
7. J.E. Forsee, and J. Aubé J. Org. Chem. 64 1999 4381 4385
8. O. Gutierrez, J. Aubé, and D.J. Tantillo J. Org. Chem. 77 2012 640 647
9. J.M. Moheney, C.R. Smith, and J.R. Johnston J. Am. Chem. Soc. 127 2005 1354 1355
10. K.F.Z. Schmidt Angew. Chem. 36 1923 511
11. K.F. Schmidt Chem. Ber. 57 1924 704 706
12. G.I. Koldobskii, V.A. Ostrovskii, and B.V. Gidaspov Russ. Chem. Rev. 47 1978 1084 1094
13. W.E. McEwan, W.E. Conrad, and C.A. Vanderwerf J. Am. Chem. Soc. 74 1952 1168 1171
14. K. Nishiyama, M. Oba, and A. Watanabe Tetrahedron 43 1987 693 700
15. H. Suzuki, and C. Nakaya Synthesis 1992 641 643
16. B.V. Rokade, and K.R. Prabhu J. Org. Chem. 77 2012 5364 5370
17. See for example G.G.K.S.N. Kumar, and K.K. Laali Tetrahedron Lett. 54 2013 965 969
18. G.G.K.S.N. Kumar, and K.K. Laali Tetrahedron Lett. 53 2012 3066 3069
19. G.G.K.S.N. Kumar, and K.K. Laali Org. Biomol. Chem. 10 2012 7347 7355
20. G. Aridoss, and K.K. Laali Tetrahedron Lett. 52 2011 6859 6864
21. G. Aridoss, and K.K. Laali J. Org. Chem. 76 2011 8088 8094