|
|
|
| Perfluoroalkanosulfonyl fluoride:A useful reagent for dehydration of aldoximes to nitriles |
| Zhao-Hua Yana, Huan Tiana, Dong-Dong Zhaoa, Hong-Ai Jina, Wei-Sheng Tianb |
a College of Chemistry, Nanchang University, Nanchang 330031, China;
b Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China |
|
|
|
|
Abstract The reaction of a variety of aldoximes with perfluoroalkanosulfonyl fluoride in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene(DBU) in dichloromethane smoothly generated the corresponding nitriles in 70%-95% yields.
|
|
Received: 02 September 2015
Published: 14 November 2015
|
| Fund:The authors thank the National Natural Science Foundation of China(No. 21362022) for financial support. |
|
Corresponding Authors:
Zhao-Hua Yan, Wei-Sheng Tian
E-mail: yanzh@ncu.edu.cn;wstian@sioc.ac.cn
|
|
|
|
| [1] |
(a) J.S. Miller, L. Manson, Designer magnets containing cyanides and nitriles, Acc. Chem. Res. 34(2001) 563-570;
|
| (b) |
M.A. Cohen, J. Sawden, N.J. Turner, Selective hydrolysis of nitriles under mild conditions by an enzyme, Tetrahedron Lett. 31(1990) 7223-7226.
|
| [2] |
F.F. Fleming, L. Yao, P.C. Ravikumar, B.C. Shook, Nitrile-containing pharmaceuticals:efficacious roles of the nitrile pharmacophore, J. Med. Chem. 53(2010) 7902-7917.
|
| [3] |
M.J. Kiefel, Synthesis:carbon with one heteroatom attached by a single bond, in:A.R. Katrizky, O. Meth-Cohn, C.W. Rees(Eds.), Comprehensive Organic Functional Group Transformations, Pergamon, Cambridge, UK, 1995, pp. 641-676.
|
| [4] |
T. Sandmeyer, Ueber die ersetzung der amidgruppe durch chlor in den aromatischen substanzen, Ber. Dtsch. Chem. Ges. 17(1884) 1633-1635.
|
| [5] |
(a) B. Movassagh, S. Shokri, Potassium fluoride doped on alumina:an efficient catalyst for conversion of aldoximes into nitriles, Synth. Commun. 35(2005) 887-890;
|
| (b) |
J.A. Campbell, G. McDougald, H. McNab, L.V.C. Rees, R.G. Tyas, Laboratoryscale synthesis of nitriles by catalysed dehydration of amides and oximes under flash vacuum pyrolysis(FVP) conditions, Synthesis 39(2007) 3179-3184;
|
| (c) |
J.K. Augustine, R. Kumar, A. Bombrun, A.B. Mandal, An efficient catalytic method for the Beckmann rearrangement of ketoximes to amides and aldoximes to nitriles mediated by propylphosphonic anhydride(T3P®), Tetrahedron Lett. 52(2011) 1074-1077;
|
| (d) |
Z. Moussa, S.A. Ahmed, A.S. ElDouhaibi, S.Y. Al-Raqa, NMR Studies and electrophilic properties of triphenylphosphine-trifluoromethanesulfonic anhydride; a remarkable dehydrating reagent system for the conversion of aldoximes to nitriles, Tetrahedron Lett. 51(2010) 1826-1831;
|
| (e) |
D. Saha, A. Saha, B.C. Ranu, Ionic liquid-promoted dehydration of aldoximes:a convenient access to aromatic, heteroaromatic and aliphatic nitriles, Tetrahedron Lett. 50(2009) 6088-6091;
|
| (f) |
L.D.S. Yadav, V.P. Srivastava, R. Patel, Bromodimethylsulfonium bromide(BDMS):a useful reagent for conversion of aldoximes and primary amides to nitriles, Tetrahedron Lett. 50(2009) 5532-5535;
|
| (g) |
R.G. Kalkhambkar, S.D. Bunge, K.K. Laali, Reaction of triflyl-imidazole with aldoximes:facile synthesis of nitriles and formation of novel aldoxime-bis(Ntriflyl)-imidazole adducts, Tetrahedron Lett. 52(2011) 5184-5187;
|
| (h) |
L. Yu, H. Li, X. Zhang, et al., Organoselenium-catalyzed mild dehydration of aldoximes:an unexpected practical method for organonitrile synthesis, Org. Lett. 16(2014) 1346-1349;
|
| (i) |
Y. Song, D. Shen, Q. Zhang, B. Chen, G. Xu, Ac2O/K2CO3/DMSO:an efficient and practical reagent system for the synthesis of nitriles from aldoximes, Tetrahedron Lett. 55(2014) 639-641(and references cited therein).
|
| [6] |
R.L. Hansen, Perfluoroalkanesulfonate esters as alkylating agents, J. Org. Chem. 29(1965) 4322-4324.
|
| [7] |
H. Vorbruggen, The Conversion of primary or secondary alcohols with nonaflyl fluoride into their corresponding inverted fluorides, Synthesis 40(2008) 1165-1174.
|
| [8] |
Z. Yan, J. Wang, W. Tian, A concise total synthesis of(-)-dehydroclausenamide utilizing the novel formation of cis-epoxide as the key step, Tetrahedron Lett. 44(2003) 9383-9384.
|
| [9] |
Z. Yan, C. Guan, Z. Yu, W. Tian, Fluoroalkanosulfonyl fluorides-mediated cyclodehydration of β-hydroxy sulfonamides and β-hydroxy thioamides to the corresponding aziridines and thiazolines, Tetrahedron Lett. 54(2013) 5788-5790.
|
| [10] |
Z. Yan, Y. Xu, W. Tian, A new and concise way to enamides by fluoroalkanosulfonyl fluoride mediated Beckmann rearrangement of α,β-unsaturated ketoximes, Tetrahedron Lett. 55(2014) 7186-7189.
|
| [11] |
M. Boruah, D. Konvar, AlCl3·3H2O/KI/H2O/CH3CN:a new alternate system for dehydration of oximes and amides in hydrated media, J. Org. Chem. 67(2002) 7138-7139.
|
| [12] |
A.V. Narsaiah, D. Sreenu, K. Nagaiah, Triphenylphosphine-I2:an efficient reagent system for the synthesis of nitriles from aldoximes, Synth. Commun. 36(2006) 137-140.
|
|
|
|
