Citation:
Zhao-Hua Yan, Huan Tian, Dong-Dong Zhao, Hong-Ai Jin, Wei-Sheng Tian. Perfluoroalkanosulfonyl fluoride:A useful reagent for dehydration of aldoximes to nitriles[J]. Chinese Chemical Letters,
;2016, 27(01): 96-98.
doi:
10.1016/j.cclet.2015.11.004
-
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.
-
-
-
[1]
[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]
[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]
[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]
[4] T. Sandmeyer, Ueber die ersetzung der amidgruppe durch chlor in den aromatischen substanzen, Ber. Dtsch. Chem. Ges. 17(1884) 1633-1635.
-
[5]
[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]
[6] R.L. Hansen, Perfluoroalkanesulfonate esters as alkylating agents, J. Org. Chem. 29(1965) 4322-4324.
-
[7]
[7] H. Vorbruggen, The Conversion of primary or secondary alcohols with nonaflyl fluoride into their corresponding inverted fluorides, Synthesis 40(2008) 1165-1174.
-
[8]
[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]
[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]
[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]
[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]
[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.
-
[1]
-
-
-
[1]
Liangfeng Yang , Liang Zeng , Yanping Zhu , Qiuan Wang , Jinheng Li . Copper-catalyzed photoredox 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN: Facile access to α-amido allenyl nitriles. Chinese Chemical Letters, 2024, 35(11): 109685-. doi: 10.1016/j.cclet.2024.109685
-
[2]
Zhi-Yuan Yue , Hua-Kai Li , Na Wang , Shan-Shan Liu , Le-Ping Miao , Heng-Yun Ye , Chao Shi . Dehydration-triggered structural phase transition-associated ferroelectricity in a hybrid perovskite-type crystal. Chinese Chemical Letters, 2024, 35(10): 109355-. doi: 10.1016/j.cclet.2023.109355
-
[3]
Wu-Yang Liu , Xin-Xiang Lei , Wen-Ji Wang , Jun-Mian Tian , Yu-Qi Gao , Jin-Ming Gao . Hyperforatone A, the 1,8-seco rearranged polycyclic polyprenylated acylphloroglucinol with a unique bicyclo[5.4.0]undecane core from Hypericum perforatum. Chinese Chemical Letters, 2025, 36(4): 110478-. doi: 10.1016/j.cclet.2024.110478
-
[4]
Ao Sun , Zipeng Li , Shuchun Li , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor. Chinese Chemical Letters, 2025, 36(3): 109972-. doi: 10.1016/j.cclet.2024.109972
-
[5]
Shaonan Liu , Shuixing Dai , Minghua Huang . The impact of ester groups on 1,8-naphthalimide electron transport material in organic solar cells. Chinese Journal of Structural Chemistry, 2024, 43(6): 100277-100277. doi: 10.1016/j.cjsc.2024.100277
-
[6]
Xuewei BA , Cheng CHENG , Huaikang ZHANG , Deqing ZHANG , Shuhua LI . Preparation and luminescent performance of Sr1-xZrSi2O7∶xDy3+ phosphor with high thermal stability. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 357-364. doi: 10.11862/CJIC.20240096
-
[7]
. . University Chemistry, 2024, 39(7): 0-0.
-
[8]
Yan Guo , Hongtao Bian , Le Yu , Jiani Ma , Yu Fang . Photochemical reaction mechanism of benzophenone protected guanosine at N7 position. Chinese Chemical Letters, 2025, 36(3): 109971-. doi: 10.1016/j.cclet.2024.109971
-
[9]
Yiran Tao , Chunlei Dai , Zhaoxiang Xie , Xinru You , Kaiwen Li , Jun Wu , Hai Huang . Redox responsive polymeric nanoparticles enhance the efficacy of cyclin dependent kinase 7 inhibitor for enhanced treatment of prostate cancer. Chinese Chemical Letters, 2024, 35(8): 109170-. doi: 10.1016/j.cclet.2023.109170
-
[10]
Hui-Juan Wang , Wen-Wen Xing , Zhen-Hai Yu , Yong-Xue Li , Heng-Yi Zhang , Qilin Yu , Hongjie Zhu , Yao-Yao Wang , Yu Liu . Cucurbit[7]uril confined phenothiazine bridged bis(bromophenyl pyridine) activated NIR luminescence for lysosome imaging. Chinese Chemical Letters, 2024, 35(6): 109183-. doi: 10.1016/j.cclet.2023.109183
-
[11]
Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
-
[12]
Zhilian Liu , Wengui Wang , Hongxiao Yang , Yu Cui , Shoufeng Wang . Ideological and Political Education Design for the Synthesis of Irinotecan Drug Intermediate 7-Ethyl Camptothecin. University Chemistry, 2024, 39(2): 89-93. doi: 10.3866/PKU.DXHX202306012
-
[13]
Hao Zhang , Haonan Qu , Ehsan Bahojb Noruzi , Haibing Li , Feng Liang . A nanocomposite film with layer-by-layer self-assembled gold nanospheres driven by cucurbit[7]uril for the selective transport of L-tryptophan and lysozyme. Chinese Chemical Letters, 2025, 36(1): 109731-. doi: 10.1016/j.cclet.2024.109731
-
[14]
Hongzhi Zhang , Hong Li , Asif Ali Haider , Junpeng Li , Zhi Xie , Hongming Jiang , Conglin Liu , Rui Wang , Jing Zhu . An unexpected role of lanthanide substitution in thermally responsive phosphors NaLnTe2O7: Eu3+ (Ln = Y and Gd). Chinese Journal of Structural Chemistry, 2025, 44(2): 100509-100509. doi: 10.1016/j.cjsc.2024.100509
-
[15]
Wujun Jian , Mong-Feng Chiou , Yajun Li , Hongli Bao , Song Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980
-
[16]
Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
-
[17]
Yijia Jiao , Yuzhu Li , Yuting Zhou , Peipei Cen , Yi Ding , Yan Guo , Xiangyu Liu . Structural evolution and zero-field SMM behaviour in ferromagnetically-coupled disk-type Co7 clusters bearing exclusively end-on azido bridges. Chinese Chemical Letters, 2024, 35(8): 109082-. doi: 10.1016/j.cclet.2023.109082
-
[18]
Huizhong Wu , Ruiheng Liang , Ge Song , Zhongzheng Hu , Xuyang Zhang , Minghua Zhou . Enhanced interfacial charge transfer on Bi metal@defective Bi2Sn2O7 quantum dots towards improved full-spectrum photocatalysis: A combined experimental and theoretical investigation. Chinese Chemical Letters, 2024, 35(6): 109131-. doi: 10.1016/j.cclet.2023.109131
-
[19]
. 第41卷第1期封面和目次. Acta Physico-Chimica Sinica, 2025, 41(1): -.
-
[20]
Huiju Cao , Lei Shi . sp1-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(703)
- HTML views(21)