Citation: Hao Liang, Zhihui Ren, Yaoyu Wang, Zhenghui Guan. One-pot green synthesis of enamides and 1,3-diynes[J]. Chinese Journal of Catalysis, ;2015, 36(1): 113-118. doi: 10.1016/S1872-2067(14)60220-5 shu

One-pot green synthesis of enamides and 1,3-diynes

1.
Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an 710127, Shaanxi, China

Corresponding author: Zhenghui Guan,
Received Date: 19 July 2014
Available Online: 2 September 2014
Fund Project: 国家自然科学基金(21272183) (21272183) 陕西省科技厅“陕西省青年科技新星”基金(2012KJXX-26). (2012KJXX-26)

A green organic synthetic method combining reductive acylation of ketoximes and oxidative coupling of terminal alkynes was developed. This novel process enables enamides and 1,3-diynes to be synthesized simultaneously in high yields and under mild conditions without the use of terminal reductants/oxidants.
- Green synthesis,
- Ketoxime,
- Terminal alkyne,
- Enamide,
- 1,3-Diyne
1. [1]
  [1] Allen S E, Walvoord R R, Padilla-Salinas R, Kozlowski M C. Chem Rev, 2013, 113: 6234
2. [2]
  [2] Saisaha P, de Boer J W, Browne W R. Chem Soc Rev, 2013, 42: 2059
3. [3]
  [3] Wu W Q, Jiang H F. Acc Chem Res, 2012, 45: 1736
4. [4]
  [4] Campbell A N, Stahl S S. Acc Chem Res, 2012, 45: 851
5. [5]
  [5] Punniyamurthy T, Velusamy S, Iqbal J. Chem Rev, 2005, 105: 2329
6. [6]
  [6] Verendel J J, Pàmies O, Diéguez M, Andersson P G. Chem Rev, 2014, 114: 2130
7. [7]
  [7] Etayo P, Vidal-Ferran A. Chem Soc Rev, 2013, 42: 728
8. [8]
  [8] Wang D S, Chen Q A, Lu S M, Zhou Y G. Chem Rev, 2012, 122: 2557
9. [9]
  [9] Xie J H, Zhu S F, Zhou Q L. Chem Rev, 2011, 111: 1713
10. [10]
  [10] Sheldon R A, Arends I W C E, Hanefeld U. Green Chemistry and Catalysis. Weinheim: Wiley-VCH, 2007. 1
11. [11]
  [11] Caron S, Dugger R W, Ruggeri S G, Ragan J A, Ripin D H B. Chem Rev, 2006, 106: 2943
12. [12]
  [12] Burkhardt E R, Matos K. Chem Rev, 2006, 106: 2617
13. [13]
  [13] Muzart J. Chem Rev, 1992, 92: 113
14. [14]
  [14] Sheldon R A. Chem Soc Rev, 2012, 41: 1437
15. [15]
  [15] Anastas P, Eghbali N. Chem Soc Rev, 2010, 39: 301
16. [16]
  [16] Horvath I T, Anastas P T. Chem Rev, 2007, 107: 2169
17. [17]
  [17] Chen M, Ren Z H, Wang Y Y, Guan Z H. Angew Chem Int Ed, 2013, 52: 14196
18. [18]
  [18] Zhao M N, Ren Z H, Wang Y Y, Guan Z H. Chem Eur J, 2014, 20: 1839
19. [19]
  [19] Zhao M N, Ren Z H, Wang Y Y, Guan Z H. Org Lett, 2014, 16: 608
20. [20]
  [20] Zhao M N, Du W, Ren Z H, Wang Y Y, Guan Z H. Eur J Org Chem, 2013, 2013: 7989
21. [21]
  [21] Zhao M N, Ren Z H, Wang Y Y, Guan Z H. Chem Commun, 2012, 48: 8105
22. [22]
  [22] Lei C H, Wang D X, Zhao L, Zhu J P, Wang M X. J Am Chem Soc, 2013, 135: 4708
23. [23]
  [23] Pankajakshan S, Xu Y H, Cheng J K, Low M T, Loh T P. Angew Chem Int Ed, 2012, 51: 5701
24. [24]
  [24] Matsubara R, Kobayashi S. Acc Chem Res, 2008, 41: 292
25. [25]
  [25] Liang H, Ren Z H, Wang Y Y, Guan Z H, Chem Eur J, 2013, 19: 9789
26. [26]
  [26] Guan Z H, Zhang Z Y, Ren Z H, Wang Y Y, Zhang X M. J Org Chem, 2011, 76: 339
27. [27]
  [27] Tang W J, Capacci A, Sarvestani M, Wei X D, Yee N K, Senanayake C H. J Org Chem, 2009, 74: 9528
28. [28]
  [28] Zhao H, Vandenbossche C P, Koenig S G, Singh S P, Bakale R P. Org Lett, 2008, 10: 505
29. [29]
  [29] Hughes R A, Thompson S P, Alcaraz L, Moody C J. J Am Chem Soc, 2005, 127: 15644
30. [30]
  [30] Haley M M, Tykwinski R R. Carbon-Rich Compounds: From Molecules to Materials. Weinheim: Wiley-VCH, 2006. 295
31. [31]
  [31] Shun A L K S, Tykwinski R R. Angew Chem Int Ed, 2006, 45: 1034
32. [32]
  [32] Diederich F, Stang P J, Tykwinski R R. Acetylene Chemistry: Chemistry, Biology and Material Science. Weinheim: Wiley-VCH, 2005. 233
33. [33]
  [33] Shi W, Lei A W. Tetrahedron Lett, 2014, 55: 2763
34. [34]
  [34] Feng X J, Zhao Z R, Yang F, Jin T N, Ma Y J, Bao M. J Organomet Chem, 2011, 696: 1479
35. [35]
  [35] Li J H, Liang Y, Zhang X D. Tetrahedron, 2005, 61: 1903
36. [36]
  [36] Doi T, Orita A, Matsuo D, Saijo R, Otera J. Synlett, 2008: 55
37. [37]
  [37] Lei A W, Srivastava M, Zhang X M. J Org Chem, 2002, 67: 1969
38. [38]
  [38] Rossi R, Carpita A, Bigelli C. Tetrahedron Lett, 1985, 26: 523
39. [39]
  [39] Zhao M N, Liang H, Ren Z H, Guan Z H. Synthesis, 2012, 44: 1501
40. [40]
  [40] Ren Z H, Zhang Z Y, Yang B Q, Wang Y Y, Guan Z H. Org Lett, 2011, 13: 5394
41. [41]
  [41] Ran L F, Ren Z H, Wang Y Y, Guan Z H. Green Chem, 2014, 16: 112
42. [42]
  [42] Zhang C, Tang C H, Jiao N. Chem Soc Rev, 2012, 41: 3464
43. [43]
  [43] Ran L F, Liang H, Guan Z H. Chin J Org Chem (冉陇飞, 梁浩, 关正辉. 有机化学), 2013, 33: 66
44. [44]
  [44] Narasaka K, Kitamura M. Eur J Org Chem, 2005: 4505
45. [45]
  [45] Reeves J T, Tan Z L, Han Z S, Li G S, Zhang Y D, Xu Y B, Reeves D C, Gonnella N C, Ma S L, Lee H, Lu B Z, Senanayake C H. Angew Chem Int Ed, 2012, 51: 1400
46. [46]
  [46] Quiclet-Sire B, Tölle N, Zafar S N, Zard S Z. Org Lett, 2011, 13:3266
47. [47]
  [47] Shi W, Luo Y D, Luo X C, Chao L, Zhang H, Wang J, Lei A W. J Am Chem Soc, 2008, 130: 14713
48. [48]
  [48] Liu Q B, Burton D J. Tetrahedron Lett, 1997, 38: 4371
49. [49]
  [49] Cai C Z, Vasella A. Helv Chim Acta, 1995, 78: 2053
50. [50]
  [50] Alper H, Saldana-Maldonado M. Organometallics, 1989, 8: 1124
1. [1]
  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
2. [2]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
3. [3]
  Tao Cao , Fang Fang , Nianguang Li , Yinan Zhang , Qichen Zhan . Green Synthesis of p-Hydroxybenzonitrile Catalyzed by Spinach Extracts under Red-Light Irradiation: Research and Exploration of Innovative Experiments for Pharmacy Undergraduates. University Chemistry, 2024, 39(5): 63-69. doi: 10.3866/PKU.DXHX202309098
4. [4]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
5. [5]
  Renxiu Zhang , Xin Zhao , Yunfei Zhang . Application of Electrochemical Synthesis in the Teaching of Organic Chemistry. University Chemistry, 2025, 40(4): 174-180. doi: 10.12461/PKU.DXHX202406116
6. [6]
  Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039
7. [7]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
8. [8]
  Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
9. [9]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
10. [10]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
11. [11]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
12. [12]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
13. [13]
  Dongheng WANG , Si LI , Shuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379
14. [14]
  Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093
15. [15]
  Zhengyu Zhou , Huiqin Yao , Youlin Wu , Teng Li , Noritatsu Tsubaki , Zhiliang Jin . Synergistic Effect of Cu-Graphdiyne/Transition Bimetallic Tungstate Formed S-Scheme Heterojunction for Enhanced Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(10): 2312010-0. doi: 10.3866/PKU.WHXB202312010
16. [16]
  Yuena Yu , Fang Fang . Microwave-Assisted Synthesis of Safinamide Methanesulfonate. University Chemistry, 2024, 39(11): 210-216. doi: 10.3866/PKU.DXHX202401076
17. [17]
  Xinghai Li , Zhisen Wu , Lijing Zhang , Shengyang Tao . Machine Learning Enables the Prediction of Amide Bond Synthesis Based on Small Datasets. Acta Physico-Chimica Sinica, 2025, 41(2): 2309041-0. doi: 10.3866/PKU.WHXB202309041
18. [18]
  Yujie WANG , Laobang WANG , Zheng ZHANG , Qi LIU , Jianping LANG . Construction of W/Cu/S cluster-based supramolecular compounds via alkynyl/sulfur cycloaddition and their third-order nonlinear optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2069-2077. doi: 10.11862/CJIC.20250129
19. [19]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
20. [20]
  Meijin Li , Xirong Fu , Xue Zheng , Yuhan Liu , Bao Li . The Marvel of NAD⁺: Nicotinamide Adenine Dinucleotide. University Chemistry, 2024, 39(9): 35-39. doi: 10.12461/PKU.DXHX202401027

Get Citation

PDF

XML

Metrics

PDF Downloads(174)
Abstract views(1165)
HTML views(104)

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