Citation: Qing-Fang Cheng, Jing-Wen Wang, Qi-Fa Wang, Zhou Liu. Intermolecular Stetter reaction of aromatic aldehydes with (E)-(2-nitrovinyl)cyclohexane induced by N-heterocyclic carbene and thiourea[J]. Chinese Chemical Letters, ;2016, 27(7): 1032-1035. doi: 10.1016/j.cclet.2016.03.007 shu

Intermolecular Stetter reaction of aromatic aldehydes with (E)-(2-nitrovinyl)cyclohexane induced by N-heterocyclic carbene and thiourea

a.
Jiangsu Key Laboratory of Marine Biotechnology, Huaihai Institute of Technology, Lianyungang 222005, China
b.
School of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, China

Corresponding author: Qi-Fa Wang, hmahdavinia@gmail.com
Received Date: 10 December 2015
Revised Date: 24 February 2016
Accepted Date: 1 March 2016
Available Online: 14 July 2016

Figures(2)

Intermolecular Stetter reaction of aromatic aldehydes with (E)-(2-nitrovinyl)cyclohexane catalyzed by thiazolium A has been developed. The reaction rate and efficiency are profoundly impacted by the presence of thiourea B. The reaction affords moderate to good yields of the Stetter product. Some factors influencing yield were discussed.
- Intermolecular Stetter reaction,
- N-heterocyclic carbene,
- Thiourea,
- Thiazolium,
- Nitroalkene,
- β-Nitro ketone
1. [1]
  H. Stetter, M. Schreckenberg. A new method for addition of aldehydes to activated double bonds[J]. Angew. Chem. Int. Ed. Engl., 1973,1281.
2. [2]
  H. Stetter. Catalyzed addition of aldehydes to activated double bonds—a new synthetic approach[J]. Angew. Chem. Int. Ed., 1976,15:639-640. doi: 10.1002/(ISSN)1521-3773
3. [3]
  M. Christmann. New developments in the asymmetric Stetter reaction[J]. Angew. Chem. Int. Ed., 2005,44:2632-2634. doi: 10.1002/(ISSN)1521-3773
4. [4]
  D. Enders, K. Breuer, J. Runsink. The first asymmetric intramolecular Stetter reaction[J]. Helv. Chim. Acta., 1996,79:1899-1902. doi: 10.1002/(ISSN)1522-2675
5. [5]
  M.S. Kerr, J.R. de Alaniz, T. Rovis. A highly enantioselective catalytic intramolecular Stetter reaction[J]. J. Am. Chem. Soc., 2002,124:10298-10299. doi: 10.1021/ja027411v
6. [6]
  C.C. Steven, T. Rovis. Catalytic asymmetric Stetter reaction onto vinylphosphine oxides and vinylphosphonates[J]. Org. Lett., 2008,10:3141-3144. doi: 10.1021/ol801047k
7. [7]
  J.R. de Alaniz, M.S. Kerr, J.L. Moore, T. Rovis. Scope of the asymmetric intramolecular Stetter reaction catalyzed by chiral nucleophilic triazolinylidene carbenes[J]. J. Org. Chem., 2008,73:2033-2040. doi: 10.1021/jo702313f
8. [8]
  J.R. de Alaniz, T. Rovis. A highly enantio- and diastereoselective catalytic intramolecular Stetter reaction[J]. J. Am. Chem. Soc., 2005,127:6284-6289. doi: 10.1021/ja0425132
9. [9]
  S.M. Mennen, J.T. Blank, M.B. Tran-Dube, J.E. Imbriglio, S.J. Miller, A peptidecatalyzed asymmetric Stetter reaction, Chem. Commun.41 (2005) 195-197.
10. [10]
  A.E. Mattson, A.R. Bharadwaj, K.A. Scheidt. The thiazolium-catalyzed sila-Stetter reaction: conjugate addition of acylsilanes to unsaturated esters and ketones[J]. J. Am. Chem. Soc., 2004,126:2314-2315. doi: 10.1021/ja0318380
11. [11]
  X.L. Hu, J.S. Johnson. Kinetic control in direct α-silyloxy ketone synthesis: a new regiospecific catalyzed cross silyl benzoin reaction[J]. Angew. Chem., 2003,115:2638-2640. doi: 10.1002/ange.200250554
12. [12]
  Q. Liu, S. Perreault, T. Rovis. Catalytic asymmetric intermolecular Stetter reaction of glyoxamides with alkylidenemalonates[J]. J. Am. Chem. Soc., 2008,130:14066-14067. doi: 10.1021/ja805680z
13. [13]
  D. Enders, J.W. Han, A. Henseler. Asymmetric intermolecular Stetter reactions catalyzed by a novel triazolium derived N-heterocyclic carbene[J]. Chem. Commun., 2008,44:3989-3991.
14. [14]
  J.M. Zhang, C. Xing, B. Tiwari, Y.G.R. Chi. Catalytic activation of carbohydrates as formaldehyde equivalents for Stetter reaction with enones[J]. J. Am. Chem. Soc., 2013,135:8113-8116. doi: 10.1021/ja401511r
15. [15]
  D.A. DiRocco, K.M. Oberg, D.M. Dalton, T. Rovis. Catalytic asymmetric intermolecular Stetter reaction of heterocyclic aldehydes with nitroalkenes: backbone fluorination improves selectivity[J]. J. Am. Chem. Soc., 2009,131:10872-10874. doi: 10.1021/ja904375q
16. [16]
  D.A. DiRocco, T. Rovis. Catalytic asymmetric intermolecular Stetter reaction of enals with nitroalkenes: enhancement of catalytic efficiency through bifunctional additives[J]. J. Am. Chem. Soc., 2011,133:10402-10405. doi: 10.1021/ja203810b
17. [17]
  A.E. Mattson, A.M. Zuhl, T.E. Reynolds, K.A. Scheidt. Direct nucleophilic acylation of nitroalkenes promoted by a fluoride anion/thiourea combination[J]. J. Am. Chem. Soc., 2006,128:4932-4933. doi: 10.1021/ja056565i
18. [18]
  G.C. Vougioukalakis, R.H. Grubbs. Synthesis and activity of ruthenium olefin metathesis catalysts coordinated with thiazol-2-ylidene ligands[J]. J. Am. Chem. Soc., 2008,130:2234-2245. doi: 10.1021/ja075849v
19. [19]
  J. Wang, H. Li, W. Duan. Organocatalytic asymmetric Michael addition of, 2, 4-pentandione to nitroolefins[J]. Org. Lett., 2005,7:4713-4716. doi: 10.1021/ol0519137
20. [20]
  T. Okino, Y. Hoashi, T. Furukawa. Enantio- and diastereoselective Michael reaction of, 1, 3-dicarbonyl copounds to nitroolefins catalyzed by a bifunctional thiourea[J]. J. Am. Chem. Soc., 2005,127:119-125. doi: 10.1021/ja044370p
21. [21]
  C.J. Wang, Z.H. Zhang, X.Q. Dong. Chiral amine-thiourea bearing multiple hydrogen bonding donors: highly efficient organocatalysts for asymmetric Michael addition of acetylacetone to nitroolefins[J]. Chem. Commun., 2008,44:1431-1433.
1. [1]
  Le Zhang , Hui-Yu Xie , Xin Li , Li-Ying Sun , Ying-Feng Han . SOMO-HOMO level conversion in triarylmethyl-cored N-heterocyclic carbene-Au(I) complexes triggered by selecting coordination halogens. Chinese Chemical Letters, 2024, 35(11): 109465-. doi: 10.1016/j.cclet.2023.109465
2. [2]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
3. [3]
  Xueru Zhao , Aopu Wang , Shimin Wang , Zhijie Song , Li Ma , Li Shao . Adsorption and visual detection of nitro explosives by pillar[n]arenes-based host–guest interactions. Chinese Chemical Letters, 2025, 36(4): 110205-. doi: 10.1016/j.cclet.2024.110205
4. [4]
  Jialin Cai , Yizhe Chen , Ruiwen Zhang , Cheng Yuan , Zeyu Jin , Yongting Chen , Shiming Zhang , Jiujun Zhang . Interfacial Pt-N coordination for promoting oxygen reduction reaction. Chinese Chemical Letters, 2025, 36(2): 110255-. doi: 10.1016/j.cclet.2024.110255
5. [5]
  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
6. [6]
  Yi Zhou , Yanzhen Liu , Yani Yan , Zonglin Yi , Yongfeng Li , Cheng-Meng Chen . Enhanced oxygen reduction reaction on La-Fe bimetal in porous N-doped carbon dodecahedra with CNTs wrapping. Chinese Chemical Letters, 2025, 36(1): 109569-. doi: 10.1016/j.cclet.2024.109569
7. [7]
  Chenhao Zhang , Qian Zhang , Yezhou Hu , Hanyu Hu , Junhao Yang , Chang Yang , Ye Zhu , Zhengkai Tu , Deli Wang . N-doped carbon confined ternary Pt₂NiCo intermetallics for efficient oxygen reduction reaction. Chinese Chemical Letters, 2025, 36(3): 110429-. doi: 10.1016/j.cclet.2024.110429
8. [8]
  Chong-Yang Shi , Jian-Xing Gong , Zhen Li , Chao Shu , Long-Wu Ye , Qing Sun , Bo Zhou , Xin-Qi Zhu . Gold-catalyzed intermolecular amination of allyl azides with ynamides: Efficient construction of 3-azabicyclo[3.1.0] scaffold. Chinese Chemical Letters, 2025, 36(2): 109895-. doi: 10.1016/j.cclet.2024.109895
9. [9]
  Quanyou Guo , Yue Yang , Tingting Hu , Hongqi Chu , Lijun Liao , Xuepeng Wang , Zhenzi Li , Liping Guo , Wei Zhou . Regulating local electron transfer environment of covalent triazine frameworks through F, N co-modification towards optimized oxygen reduction reaction. Chinese Chemical Letters, 2025, 36(1): 110235-. doi: 10.1016/j.cclet.2024.110235
10. [10]
  Songtao Cai , Liuying Wu , Yuan Li , Soham Samanta , Jinying Wang , Bing Liu , Feihu Wu , Kaitao Lai , Yingchao Liu , Junle Qu , Zhigang Yang . Intermolecular hydrogen-bonding as a robust tool toward significantly improving the photothermal conversion efficiency of a NIR-II squaraine dye. Chinese Chemical Letters, 2024, 35(4): 108599-. doi: 10.1016/j.cclet.2023.108599
11. [11]
  Kun Tang , Fen Su , Shijie Pan , Fengfei Lu , Zhongfu Luo , Fengrui Che , Xingxing Wu , Yonggui Robin Chi . Enones from aldehydes and alkenes by carbene-catalyzed dehydrogenative couplings. Chinese Chemical Letters, 2024, 35(9): 109495-. doi: 10.1016/j.cclet.2024.109495
12. [12]
  Yuhan Liu , Jingyang Zhang , Gongming Yang , Jian Wang . Highly enantioselective carbene-catalyzed δ-lactonization via radical relay cross-coupling. Chinese Chemical Letters, 2025, 36(1): 109790-. doi: 10.1016/j.cclet.2024.109790
13. [13]
  Rui Wang , Yang Liang , Julius Rebek Jr. , Yang Yu . Stabilization and detection of labile reaction intermediates in supramolecular containers. Chinese Chemical Letters, 2024, 35(6): 109228-. doi: 10.1016/j.cclet.2023.109228
14. [14]
  Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Yongfeng Wang . Recent progress on surface chemistry Ⅰ: Assembly and reaction. Chinese Chemical Letters, 2024, 35(12): 110055-. doi: 10.1016/j.cclet.2024.110055
15. [15]
  Tiantian Long , Hongmei Luo , Jingbo Sun , Fengniu Lu , Yi Chen , Dong Xu , Zhiqin Yuan . Carbonization-engineered ultrafast chemical reaction on nanointerface. Chinese Chemical Letters, 2025, 36(3): 109728-. doi: 10.1016/j.cclet.2024.109728
16. [16]
  Yi Zhang , Biao Wang , Chao Hu , Muhammad Humayun , Yaping Huang , Yulin Cao , Mosaad Negem , Yigang Ding , Chundong Wang . Fe–Ni–F electrocatalyst for enhancing reaction kinetics of water oxidation. Chinese Journal of Structural Chemistry, 2024, 43(2): 100243-100243. doi: 10.1016/j.cjsc.2024.100243
17. [17]
  Xianxu Chu , Lu Wang , Junru Li , Hui Xu . Surface chemical microenvironment engineering of catalysts by organic molecules for boosting electrocatalytic reaction. Chinese Chemical Letters, 2024, 35(8): 109105-. doi: 10.1016/j.cclet.2023.109105
18. [18]
  Kebo Xie , Qian Zhang , Fei Ye , Jungui Dai . A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides. Chinese Chemical Letters, 2024, 35(6): 109028-. doi: 10.1016/j.cclet.2023.109028
19. [19]
  Zhao Li , Huimin Yang , Wenjing Cheng , Lin Tian . Recent progress of in situ/operando characterization techniques for electrocatalytic energy conversion reaction. Chinese Chemical Letters, 2024, 35(9): 109237-. doi: 10.1016/j.cclet.2023.109237
20. [20]
  Kunsong Hu , Yulong Zhang , Jiayi Zhu , Jinhua Mai , Gang Liu , Manoj Krishna Sugumar , Xinhua Liu , Feng Zhan , Rui Tan . Nano-engineered catalysts for high-performance oxygen reduction reaction. Chinese Chemical Letters, 2024, 35(10): 109423-. doi: 10.1016/j.cclet.2023.109423

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(735)
HTML views(19)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142