Citation: Shen Xuqian, Cao Xihan, Zheng Wanbin, Yang Jun, Shi Yongsen, Hu Jingang, Wu Xiangmei, Yan Guobing. Recent Progress in the Research of Acetone in Coupling Reactions[J]. Chinese Journal of Organic Chemistry, ;2017, 37(2): 349-355. doi: 10.6023/cjoc201607043 shu

Recent Progress in the Research of Acetone in Coupling Reactions

Department of Chemistry, Lishui University, Lishui 323000

Corresponding author: Yan Guobing, gbyan@lsu.edu.cn
Received Date: 28 July 2016
Revised Date: 15 September 2016

Fund Project: the National Natural Science Foundationof China 21572094

Figures(7)

Acetone is the simplest ketone, which has the typical reaction of ketones. In this paper, the recent development centering the coupling reactions of acetone including the formation of carbon-carbon, carbon-heteroatom bonds and the discussion of reaction mechanism, is reviewed.
- acetone,
- coupling reaction,
- reaction mechanism
1. [1]
  (a) Pan, J.; Wang, Y.; Chen, S.; Zhang, X.; Wang Y.; Zhou, Z. Tetrahedron 2016, 72, 240.
  (b) Wang, F.; Liu, Y.; Qi, Z.; Dai, W.; Li, X. Tetrahedron Lett. 2014, 55, 6399.
  (c) Lu, A.; Wu, R.; Wang, Y.; Wu, G.; Zhou, Z.; Fang, J.; Tang, C. J. Org. Chem. 2011, 76, 3872.
  (d) Onodera, G.; Matsumoto, H.; Nishibayashi, Y.; Uemura, S. Organometallics 2005, 24, 5799.
  (e) Özkar, S.; Finke, R. G. J. Am. Chem. Soc. 2005, 127, 4800.
  (f) Noland, W. E.; Konkel, M. J.; Konkel, L. C.; Pearce, B. C. J. Org. Chem. 1996, 61, 451.
2. [2]
  For selected applications, see: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
  (b) Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450.
  (c) Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534.
  (d) Bellina, F.; Rossi, R. Chem. Rev. 2010, 110, 1082.
  (e) Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2013, 46, 236.
3. [3]
  (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108.
  (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382.
  (c) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. 1997, 36, 1740.
4. [4]
  (a) Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234.
  (b) Shao, Z.; Zhang, H. Chin. J. Org. Chem. 2005, 25, 282.
  (c) Gong, J. F.; Xu, C.; Wu, Y. J. Prog. Chem. 2006, 18, 752.
5. [5]
  (a) Chobanian, H. R.; Liu, P.; Chioda, M. D.; Guo, Y.; Lin, L. S. Tetrahedron Lett. 2007, 48, 1213.
  (b) Su, W. P.; Raders, S.; Verkade, J. G.; Liao, X. B.; Hartwig, J. F. Angew. Chem., Int. Ed. 2006, 45, 5852.
  (c) Liu, P.; Lanza, Jr., T. J.; Jewell, J. P.; Jones, C. P.; Hagmann, W. K.; Lin, L. S. Tetrahedron Lett. 2003, 44, 8869.
  (d) Kosugi, M.; Suzuki, M.; Hagiwara, I.; Goto, K.; Saitoh, K.; Migita, T. Chem. Lett. 1982, 939.
6. [6]
  Hesp, K. D.; Lundgren, R. J.; Stradiotto, M. J. Am. Chem. Soc. 2011, 133, 5194. doi: 10.1021/ja200009c
7. [7]
  Alsabeh, P. G.; Stradiotto, M. Angew. Chem., Int. Ed. 2013, 52, 1.
8. [8]
  Rotta-Loria, N. L.; Borzenko, A.; Alsabeh, P. G.; Lavery, C. B.; Stradiotto, M. Adv. Synth. Catal. 2015, 357, 100. doi: 10.1002/adsc.v357.1
9. [9]
  Ackermann, L.; Mehta, V. P. Chem. Eur. J. 2012, 18, 10230. doi: 10.1002/chem.201201394
10. [10]
  Li, P.; Lü, B.; Fu, C.; Ma, S. Adv. Synth. Catal. 2013, 355, 1255. doi: 10.1002/adsc.v355.7
11. [11]
  (a) Cartney, D.; Guiry, J. P. Chem. Soc. Rev. 2011, 40, 5122.
  (b) Ana, R.; Pathak, T. P.; Sigman, M. Chem. Rev. 2011, 111, 1417.
12. [12]
  Gäbler, C.; Korb, M.; Schaarschmidt, D.; Hildebrandt, A.; Lang, H.; Adv. Synth. Catal. 2014, 356, 2979. doi: 10.1002/adsc.201400235
13. [13]
  (a) MacQueen, P. M.; Chisholm, A. J.; Hargreaves, B. K. V.; Stradiotto, M. Chem. Eur. J. 2015, 21, 11006.
  (b) Schranck, J.; Rotzler, J. Org. Process Res. Dev. 2015, 19, 1936.
14. [14]
  Fu, W. C.; So, C. M.; Chow, W. K.; Yuen, O. Y.; Kwong, F. Y. Org. Lett. 2015, 17, 4612. doi: 10.1021/acs.orglett.5b02344
15. [15]
  Schranck, J.; Tlili, A.; Alsabeh, P. G.; Neumann, H.; Stradiotto, M.; Beller, M. Chem. Eur. J. 2013, 19, 12624. doi: 10.1002/chem.201302590
16. [16]
  For selective reviews, see: (a) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519.
  (b) Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163.
  (c) Gansäuer, A.; Bluhm, H. Chem. Rev. 2000, 100, 2771.
  (d) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94.
  (e) Studer, A. Chem. Soc. Rev. 2004, 33, 263.
  (f) Brown, S. S.; Stutz, J. Chem. Soc. Rev. 2012, 41, 6405.
  (g) zirakis, M. D.; Orfanopoulos, M. Chem. Rev. 2013, 113, 5262.
  (h) Dénès, F.; Schiesser, C. H.; Renaud, P. Chem. Soc. Rev. 2013, 42, 7900.
17. [17]
  (a) Norrish, R. G.; Bond, C. H. Nature 1936, 138, 1016.
  (b) Büchi, G.; Inman, C. G.; Lipinsky, E. S. J. Am. Chem. Soc. 1954, 76, 4327.
  (c) Nau, W. M.; Cozens, F. L.; Scaiano, J. C. J. Am. Chem. Soc. 1996, 118, 2275.
  (d) Reusch, W. J. Org. Chem. 1962, 27, 1882.
  (e) Majerski, K. M.; Pavlović, D.; Kulyk, M. Š. J. Org. Chem. 1993, 58, 252.
  (f) Chung, W.-S.; Ho, C.-C. Chem. Commun. 1997, 317.
  (g) Toltl, N. P.; Leigh, W. J. Organometallics 1996, 15, 2554.
  (h) Ghandi, K.; Addison-Jones, B.; Brodovitch, J.-C.; McCollum, B. M.; McKenzie, I.; Percival, P. W. J. Am. Chem. Soc. 2003, 125, 9594.
  (i) Shiraishi, Y.; Tsukamoto, D.; Hirai, T. Org. Lett. 2008, 10, 3117.
  (j) Tsukamoto, D.; Shiraishi, Y.; Hirai, T. J. Org. Chem. 2010, 75, 1450.
18. [18]
  Schweitzer-Chaput, B.; Demaerel, B. J.; Engler, H.; Klussmann, M. Angew. Chem., Int. Ed. 2014, 53, 8737. doi: 10.1002/anie.201401062
19. [19]
  (a) Xia, X.-F.; Zhu, S-L.; Zeng, M.; Gu, Z.; Wang, H.; Li, W. Tetrahedron 2015, 71, 6099.
  (b) oess, E.; Karanestora1, S.; Bosnidou1, A.-E.; Schweitzer-haput, B.; Hasenbeck, M.; Klussmann, M. Synlett 2015, 1973.
20. [20]
  Chu, X.-Q.; Meng, H.; Zi, Y.; Xu, X.-P.; Ji, S.-J. Chem. Eur. J. 2014, 20, 17198. doi: 10.1002/chem.201404463
21. [21]
  Zhu, L.; Chen, H.; Wang, Z.; Li, C. Org. Chem. Front. 2014, 1, 1299. doi: 10.1039/C4QO00256C
22. [22]
  Lan, X.-W.; Wang, N.-X.; Zhang, W.; Wen, J.-L.; Bai, C.-B.; Xing, Y.; Li, Y.-H. Org. Lett. 2015, 17, 4460. doi: 10.1021/acs.orglett.5b02116
23. [23]
  Wang, C.; Lei, S.; Cao, H.; Qiu, S.; Liu, J.; Deng, H.; Yan, C. J. Org. Chem. 2015, 80, 12725. doi: 10.1021/acs.joc.5b02417
24. [24]
  Yan, G.; Borah, A. J.; Wang, L.; Pan, Z.; Chen, C.; Shen, X.; Wu, X. Tetrahedron Lett. 2015, 56, 4305. doi: 10.1016/j.tetlet.2015.05.059
25. [25]
  Shen, X.; Borah, A. J.; Cao, X.; Pan, W.; Yan, G.; Wu, X. Tetrahedron Lett. 2015, 56, 6484. doi: 10.1016/j.tetlet.2015.10.006
1. [1]
  Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
2. [2]
  Ronghao Zhao , Yifan Liang , Mengyao Shi , Rongxiu Zhu , Dongju Zhang . Investigation into the Mechanism and Migratory Aptitude of Typical Pinacol Rearrangement Reactions: A Research-Oriented Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 305-313. doi: 10.3866/PKU.DXHX202309101
3. [3]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
4. [4]
  Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010
5. [5]
  Aili Feng , Xin Lu , Peng Liu , Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072
6. [6]
  Guowen Xing , Guangjian Liu , Le Chang . Five Types of Reactions of Carbonyl Oxonium Intermediates in University Organic Chemistry Teaching. University Chemistry, 2025, 40(4): 282-290. doi: 10.12461/PKU.DXHX202407058
7. [7]
  Ling Fan , Meili Pang , Yeyun Zhang , Yanmei Wang , Zhenfeng Shang . Quantum Chemistry Calculation Research on the Diels-Alder Reaction of Anthracene and Maleic Anhydride: Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 133-139. doi: 10.3866/PKU.DXHX202309024
8. [8]
  Jiabo Huang , Quanxin Li , Zhongyan Cao , Li Dang , Shaofei Ni . Elucidating the Mechanism of Beckmann Rearrangement Reaction Using Quantum Chemical Calculations. University Chemistry, 2025, 40(3): 153-159. doi: 10.12461/PKU.DXHX202405172
9. [9]
  Lewang Yuan , Yaoyao Peng , Zong-Jie Guan , Yu Fang . 二维共价有机框架作为光催化剂在有机合成中的研究进展. Acta Physico-Chimica Sinica, 2025, 41(8): 100086-. doi: 10.1016/j.actphy.2025.100086
10. [10]
  Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V₂O₅/TiO₂ catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210
11. [11]
  Qian Huang , Zhaowei Li , Jianing Zhao , Ao Yu . Quantum Chemical Calculations Reveal the Details Below the Experimental Phenomenon. University Chemistry, 2024, 39(3): 395-400. doi: 10.3866/PKU.DXHX202309018
12. [12]
  Yong Wang , Yingying Zhao , Boshun Wan . Analysis of Organic Questions in the 37th Chinese Chemistry Olympiad (Preliminary). University Chemistry, 2024, 39(11): 406-416. doi: 10.12461/PKU.DXHX202403009
13. [13]
  Mingyang Men , Jinghua Wu , Gaozhan Liu , Jing Zhang , Nini Zhang , Xiayin Yao . 液相法制备硫化物固体电解质及其在全固态锂电池中的应用. Acta Physico-Chimica Sinica, 2025, 41(1): 2309019-. doi: 10.3866/PKU.WHXB202309019
14. [14]
  Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
15. [15]
  Lancanghong Chen , Xingtai Yu , Tianlei Zhao , Qizhi Yao . Exploration of Abnormal Phenomena in Iodometric Copper Quantitation Experiment. University Chemistry, 2025, 40(7): 315-320. doi: 10.12461/PKU.DXHX202408089
16. [16]
  Hongmei Chai , Yixia Ren , Xiangyang Hou , Long Tang , Jiawei Xie . 智能手机光传感的“丙酮碘化反应”实验改进. University Chemistry, 2025, 40(6): 193-200. doi: 10.12461/PKU.DXHX202407086
17. [17]
  Heng Zhang . Determination of All Rate Constants in the Enzyme Catalyzed Reactions Based on Michaelis-Menten Mechanism. University Chemistry, 2024, 39(4): 395-400. doi: 10.3866/PKU.DXHX202310047
18. [18]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
19. [19]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
20. [20]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078

Get Citation

PDF

XML

Metrics

PDF Downloads(17)
Abstract views(2738)
HTML views(614)

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