Citation: Yaghoub Sarrafi, Marzieh Sadatshahabi, Kamal Alimohammadi. A mild, simple and efficient method for selective α-monobromination of 1,3-diketones and β-keto-esters using pyridinium bromochromate[J]. Chinese Chemical Letters, ;2009, 20(4): 393-396. doi: 10.1016/j.cclet.2008.11.022 shu

A mild, simple and efficient method for selective α-monobromination of 1,3-diketones and β-keto-esters using pyridinium bromochromate

Department of Chemistry, Mazandaran University, Babolsar, Iran

Received Date: 17 September 2008

Fund Project: Financial support from the Research Council of Mazandaran University is gratefully acknowledged.

Pyridinium bromochromate has been found to be a highly efficient and selective reagent for the α-monobromination of 1,3-diketones and β-keto-esters in the absence of base, Lewis acid, or other catalyst. The products were formed in high to excellent yields under mild reaction conditions and in short reaction times
- α-Monobromination,
- β-Keto-esters,
- Pyridinium bromochromate,
- 1,
- 3-Diketones
1. [1]
  Xian Ping DAI , Xing Zhou LI , Zhi Bing ZHENG , Song LI . Synthesis and Biological Evaluation of Novel 1, 5-Diarylpyrazole-3-carboxamide Compounds as Inhibitors of ALK5. Chinese Chemical Letters, 2006, 17(5): 609-612.
2. [2]
  Zhi Wen Gao , Shou Feng Wang , Chun Gu Xia . Synthesis of propylene carbonate from urea and 1,2-propanediol. Chinese Chemical Letters, 2009, 20(2): 131-135. doi: 10.1016/j.cclet.2008.10.038
3. [3]
  Zheng He PENG , Xiao Ming REN , Chen Jie FANG , Bin Guang ZHANG , Ju Tang SUEN . Synthesis and Spectroscopic Characteriration of Transition MetalComplexes of Maleionitriledithiolene and 1,10-Phenanthroline. Chinese Chemical Letters, 1999, 10(3): 263-266.
4. [4]
  Zhen QIAO , Xue Yan SHI , Qing Hua BIAN , Shi Cong HOU , Min WANG . Asymmetric Induction of Chiral 1,1'-Bis (oxazolinyl) ferrocenes as Ligands in Metal-Catalyzed Cyclopropanation and Diels-Alder Reactions. Chinese Chemical Letters, 2004, 15(9): 1015-1018.
5. [5]
  WU Zhen-Dong . Synthesis, Structure and Photoluminescence of a New Pb(II) Coordination Polymer [Pb(1, 4-chdc)(L)]_n·nH₂OBased on a Flexible 1,4-Cyclohexanedicarboxylic Acid. Chinese Journal of Structural Chemistry, 2016, 35(5): 753-757. doi: 10.14102/j.cnki.0254-5861.2011-0958
6. [6]
  Ge Fang , Zhu Yanyun , Xian Mo , Wang Xiaowu . Iron-Based Complexes: Applications in 1,3-Diene Monomers Homogeneous Coordination-Insertion Polymerization Catalysis. Chemistry, 2020, 83(5): 404-417.
7. [7]
  Khodabakhsh Niknam , Dariush Saberi , Mojtaba Baghernejad . Silica-bonded S-sulfonic acid a recyclable catalyst for the synthesis of coumarins. Chinese Chemical Letters, 2009, 20(12): 1444-1448. doi: 10.1016/j.cclet.2009.06.039
8. [8]
  Wang Binbin , Liu Lei , Zhang Yuanyuan , Shen Liangjun , Wang Lejia , Chen Aibinga , Feng Haobin , Xiao Xunwen . Novel Diaryquioxaline Derivatives with Aggregation-Induced Emission Characteristics for Turn-On Detection of Hg²⁺. Chemistry, 2018, 81(6): 525-530.
9. [9]
  Hong She Wang Wei Xing Zhao . Magnesium bistrifluoromethanesulfonimide as an efficient catalyst for the hydroalkylation of aromatic olefins with 1,3-diketones under solvent-free conditions. Chinese Chemical Letters, 2011, 22(8): 911-914. doi: 10.1016/j.cclet.2011.01.036
10. [10]
  Zhi-Bo Jiang , Wei-Xia Song , Jian-Gong Shi . Two 1-(6'-O-acyl-β-D-glucopyranosyl)pyridinium-3-carboxylates from the flower buds of Lonicera japonica. Chinese Chemical Letters, 2015, 26(1): 69-72. doi: 10.1016/j.cclet.2014.10.011
11. [11]
  Yu-Hai Liu , Jia-Jia Shi , Dan-Qing Gao , Yun-Long Gao , Ran Guo , Xiao-Feng Ling , Shi-Fu Weng , Yi-Zhuang Xu , Isao Noda , Jin-Guang Wu . Interactions between pyridinium and Nd³⁺. Chinese Chemical Letters, 2015, 26(2): 182-186. doi: 10.1016/j.cclet.2015.01.014
12. [12]
  Sima Kalhor , Javad Safaei-Ghomi . A convenient synthesis of 2-aminocyclohex-1-ene-1-carboxylic esters by FeCl₃/SiO₂ nanoparticles as robust and efficient catalyst. Chinese Chemical Letters, 2015, 26(6): 735-738. doi: 10.1016/j.cclet.2015.01.035
13. [13]
  Peng LI , Jie Cheng XU . 1-Ethyl-2-Fluoro Pyridinium Salt:A Highly Efficient Coupling Reagents for Sterically Hindered Peptide Synthesis. Chinese Chemical Letters, 2000, 11(5): 377-380.
14. [14]
  Chun Hui HUANG , Xiao Yan ZHU , Ke Zhi WANG , Guang Xian XU , Yu XU Yuan , Qi LIU , Pei ZHANG , Xu Peng WANG . STUDIES ON LANGMUIR-BLODGETT FILM OF METAL COMPLEXES(Ⅰ)-PREPARATION AND CHARACTERIZATION OF THE LB FILM OF N-HEXADECYL PYRIDINIUM TETRAKIS（1-PHENYL-3-METHYL-4-BENZOYL-PYRAZOL-5-ONE）EUROPIUM, C₅H₅NC₁₆H₃₃Eu(PMBP)₄. Chinese Chemical Letters, 1991, 3(9): 741-744.
15. [15]
  Li Ling Hao , Jun Fen Li , Pei Hua Lin , Rui Feng Dong , Du Xin Li , Shao Min Shuang , Chuan Dong . A novel carbazole-based fluorescent probe: 3,6-Bis-[(N-ethylcarbazole-3-yl)-propene-1-keto]-N-ethylcarbazole. Chinese Chemical Letters, 2010, 21(1): 9-12. doi: 10.1016/j.cclet.2009.07.003
16. [16]
  Mohammad Hossein Mosslemin , Nasim Shams , Hossein Esteghamat , Hossein Anaraki-Ardakani . An efficient synthesis of functionalized tetrahydro-1H-indeno[2, 1-c]pyridine derivatives by a PPh₃-promoted condensation reaction between acetylene esters and 1,3-dioxo-N-aryl-2,3- dihydro-1H-indene-2-carboxamides. Chinese Chemical Letters, 2013, 24(12): 1095-1098.
17. [17]
  Sheng-Jian Jia , Da-Ming Du . Enantioselective chlorination ofb-keto esters and amides catalyzed by chiral copper(Ⅱ) complexes of squaramide-linked bisoxazoline ligand. Chinese Chemical Letters, 2014, 25(11): 1479-1484. doi: 10.1016/j.cclet.2014.06.023
18. [18]
  Kong Shengnan , Malik Abaid Ullah , Qian Xuefeng , Shu Mouhai , Xiao Wende . Asymmetric Hydrogenation of β-Keto Esters Catalyzed by Ruthenium Species Supported on Porous Organic Polymer. Chinese Journal of Organic Chemistry, 2018, 38(3): 656-664. doi: 10.6023/cjoc201709018
19. [19]
  Jin Cui , Ming Jie Zhang , Xiang Qian Wang , Nai Jing Cui . The setereoselective preparation of β-keto esters using baker's yeast in the presence of rice wine koji. Chinese Chemical Letters, 2008, 19(3): 311-313. doi: 10.1016/j.cclet.2008.01.005

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