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Synlett 2019; 30(02): 181-184
DOI: 10.1055/s-0037-1610308
DOI: 10.1055/s-0037-1610308
letter
Ph3P/I–-Promoted Dichlorination or Dibromination of Epoxides with XCH2CH2X (X = Cl or Br)
We thank the National Basic Research Program of China (2015CB931903), the National Natural Science Foundation (21421002, 21472222, 21502214, 21672242, 81273537), the Chinese Academy of Sciences (XDA02020105, XDA02020106), the Key Research Program of Frontier Sciences (CAS) (QYZDJSSW-SLH049), the Key Project of Hunan Province Science and Technology Department (2016DK2001), the Key Project of Hunan Provincial Education Department (No. 17A190), the Zhengxiang Scholar Program of the University of South China, Hunan Provincial Hengyang City Joint Fund (2017JJ4050), and the Key Project of Hengyang Science and Technology Department(2017KJ166) for financial support.Further Information
Publication History
Received: 03 September 2018
Accepted after revision: 30 September 2018
Publication Date:
19 December 2018 (online)
Abstract
Ph3P/I–-promoted dichlorination and dibromination of epoxides by using XCH2CH2X (X = Cl or Br) as the halogen source and reaction solvent is described. All reagents are widely available and easy to handle, and mild conditions and operational simplicity make this protocol attractive.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610308.
- Supporting Information
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References
- 1a Davies J, Caseley JC. Pestic. Sci. 1999; 55: 1043
- 1b Vaillancourt FH, Yeh E, Vosburg DA, Garneau-Tsodikova S, Walsh CT. Chem. Rev. 2006; 106: 3364
- 1c Chung W.-j, Vanderwal CD. Angew. Chem. Int. Ed. 2016; 55: 4396
- 1d Weichold V, Milbredt D, van Pee K.-H. Angew. Chem. Int. Ed. 2016; 55: 6374
- 2a Cresswell AJ, Eey ST. C, Denmark SE. Angew. Chem. Int. Ed. 2015; 54: 15642
- 2b Ren J, Tong R. Org. Biomol. Chem. 2013; 11: 4312
- 2c Kamada Y, Kitamura Y, Tanaka T, Yoshimitsu T. Org. Biomol. Chem. 2013; 11: 1598
- 3a Sonnet PE, Oliver JE. J. Org. Chem. 1976; 41: 3279
- 3b Iranpoor N, Firouzabadi H, Aghapour G, Nahid A. Bull. Chem. Soc. Jpn. 2004; 77: 1885
- 3c Iranpoor N, Firouzabadi H, Azadi R, Ebrahimzadeh F. Can. J. Chem. 2006; 84: 69
- 3d Yoshimitsu T, Fukumoto N, Tanaka T. J. Org. Chem. 2009; 74: 696
- 3e De Andrade VS. C, De Mattos MC. S. Synthesis 2016; 48: 1381
- 4a Appel R. Angew. Chem., Int. Ed. Engl. 1975; 14: 801
- 4b van Kalkeren HA, van Delft FL, Rutjes FP. J. T. Pure Appl. Chem. 2013; 85: 817
- 4c de Andrade VS. C, de Mattos MC. S. Curr. Org. Synth. 2015; 12: 309
- 5a Yoshimitsu T, Fukumoto N, Nakatani R, Kojima N, Tanaka T. J. Org. Chem. 2010; 75: 5425
- 5b Yoshimitsu T, Nakatani R, Kobayashi A, Tanaka T. Org. Lett. 2011; 13: 908
- 6a Denton RM, An J, Adeniran B. Chem. Commun. 2010; 46: 3025
- 6b Denton RM, Tang X, Przeslak A. Org. Lett. 2010; 12: 4678
- 6c Denton RM, An J, Adeniran B, Blake AJ, Lewis W, Poulton AM. J. Org. Chem. 2011; 76: 6749
- 6d An J, Tang X, Moore J, Lewis W, Denton RM. Tetrahedron 2013; 69: 8769
- 7 Xia X, Toy PH. Beilstein J. Org. Chem. 2014; 10: 1397
- 8 Cleveland AH, Fronczek FR, Kartika R. J. Org. Chem. 2018; 83: 3367
- 9a Maryanoff BE, Reitz AB. Chem. Rev. 1989; 89: 863
- 9b Werner T. Adv. Synth. Catal. 2009; 351: 1469
- 9c Marsden SP. Nat. Chem. 2009; 1: 685
- 9d Byrne PA, Gilheany DG. Chem. Soc. Rev. 2013; 42: 6670
- 9e Bayne JM, Stephan DW. Chem. Soc. Rev. 2016; 45: 765
- 10a Deng Z, Lin J.-H, Xiao J.-C. Nat. Commun. 2016; 7: 10337
- 10b Deng Z, Lin J.-H, Cai J, Xiao J.-C. Org. Lett. 2016; 18: 3206
- 10c Deng Z, Liu C, Zeng X.-L, Lin J.-H, Xiao J.-CJ. Org. Chem. 2016; 81: 12084
- 10d Zeng X.-L, Deng Z.-Y, Liu C, Zhao G, Lin J.-H, Zheng X, Xiao J.-C. J. Fluorine Chem. 2017; 193: 17
- 11a Chen J, Lin J.-H, Xiao J.-C. Org. Lett. 2018; 20: 3061
- 11b Chen J, Lin J.-H, Xiao J.-C. Chem. Commun. 2018; 54: 7034
- 11c Zhang W, Chen J, Lin J.-H, Xiao J.-C, Gu Y.-C. iScience 2018; 5: 110
- 12 Hine J, Brader WH. J. Am. Chem. Soc. 1955; 77: 361
- 13 Schubert WM, Steadly H, Rabinovitch BS. J. Am. Chem. Soc. 1955; 77: 5755
- 14a Cotton FA, Kibala PA. J. Am. Chem. Soc. 1987; 109: 3308
- 14b Morcillo SP, Alvarez de Cienfuegos L, Mota AJ, Justicia J, Robles R. J. Org. Chem. 2011; 76: 2277
- 15 Pathak G, Rokhum L. ACS Comb. Sci. 2015; 17: 483