Citation: Ting-Ting Li, Cui Xu, Chang-Bin Xiang, Jie Yan. An efficient chlorination of aromatic compounds using a catalytic amount of iodobenzene[J]. Chinese Chemical Letters, ;2013, 24(6): 535-538. shu

An efficient chlorination of aromatic compounds using a catalytic amount of iodobenzene

1.
a College of Chemical Engineering and Materials Sciences, Zhejiang University of Technology, Hangzhou 310032, China;
2.
b Foreign Language School, Zhejiang Shuren University, Hangzhou 310015, China

Corresponding author: Jie Yan,
Received Date: 6 January 2013
Available Online: 19 March 2013

An efficient method was developed for chlorination of aromatic compounds with electron-donating groups using iodobenzene as the catalyst and m-chloroperbenzoic acid as the terminal oxidant in the presence of 4-methylbenzenesulfonic acid in THF at room temperature for 24 h, and a series of the monochlorinated compounds was obtained in good yields. In this protocol, the catalyst iodobenzene was first oxidized into the hypervalent iodine intermediate, which then treated with lithium chloride and finally reacted with aromatic compounds to form the chlorinated compounds.
- Hypervalent iodine intermediate,
- Chlorination,
- Catalytic oxidation,
- Synthesis
1. [1]
  [1] P.J. Stang, V.V. Zhdankin, Organic polyvalent iodine compounds, Chem. Rev. 96 (1996) 1123-1178.
2. [2]
  [2] V.V. Zhdankin, P.J. Stang, Recent developments in the chemistry of polyvalent iodine compounds, Chem. Rev. 102 (2002) 2523-2584.
3. [3]
  [3] T. Dohi, Y. Kita, Hypervalent iodine reagents as a new entrance to organocatalysts, Chem. Commun. (2009) 2073-2085.
4. [4]
  [4] M. Ochiai, Nucleophilic vinylic substitutions of l3-vinyliodanes, J. Organomet. Chem. 611 (2000) 494-508.
5. [5]
  [5] T. Okuyama, Solvolysis of vinyl iodonium salts. New insights into vinyl cation intermediates, Acc. Chem. Res. 35 (2002) 12-18.
6. [6]
  [6] M. Frigerio, M. Santagostino, A mild oxidizing reagent for alcohols and 1,2-diols: o-iodoxybenzoic acid (IBX) in DMSO, Tetrahedron Lett. 35 (1994) 8019-8022.
7. [7]
  [7] K.C. Nicolaou, Y.L. Zhong, P.S. Baran, New synthetic technology for the rapid construction of novel heterocycles—part 1: the reaction of Dess-Martin periodinane with anilides and related compounds, Angew. Chem. Int. Ed. 39 (2000) 622-625.
8. [8]
  [8] T. Dohi, M. Ito, N. Yamaoka, et al., Hypervalent iodine(Ⅲ): selective and efficient single-electron-transfer (SET) oxidizing agent, Tetrahedron 65 (2009) 10797-10815.
9. [9]
  [9] M. Traoré, S. Ahmed-Ali, M. Peuchmaur, et al., Hypervalent iodine(Ⅲ)-mediated tandem oxidative reactions: application for the synthesis of bioactive polyspirocyclohexa-2,5-dienones, Tetrahedron 66 (2010) 5863-5872.
10. [10]
  [10] M. Arisawa, N.G. Ramesh, M. Nakaima, et al., Hypervalent iodine(Ⅲ)-induced intramolecular cyclization of a-(aryl) alkyl-b-dicarbonyl compounds: a convenient synthesis of benzannulated and spirobenzannulated compounds, J. Org. Chem. 66 (2001) 59-65.
11. [11]
  [11] H. Tohma, H. Morioka, S. Takizawa, et al., Efficient oxidative biaryl coupling reaction of phenol ether derivatives using hypervalent iodine(Ⅲ) reagents, Tetrahedron 57 (2001) 345-352.
12. [12]
  [12] H. Hamamoto, G. Anilkumar, H. Tohma, et al., A novel and useful oxidative intramolecular coupling reaction of phenol ether derivatives on treatment with a combination of hypervalent iodine(Ⅲ) reagent and heteropoly acid, Chem. Eur. J. 8 (2002) 5377-5383.
13. [13]
  [13] L. Shi, Y.J. Kim, D.Y. Gin, C2-acyloxyglycosylation with glycal donors, J. Am. Chem. Soc. 123 (2001) 6939-6940.
14. [14]
  [14] J. Barluenga, M. Maro-Arias, F. Gonzá lez-Bobes, et al., Reaction of alkenes with hydrogen peroxide and sodium iodide: a nonenzymatic biogenic-like approach to iodohydrins, Chem. Eur. J. 10 (2004) 1677-1682.
15. [15]
  [15] K.C. Nicolaou, K. Sugita, P.S. Baran, et al., Iodine(V) reagents in organic synthesis. Part 1. Synthesis of polycyclic heterocycles via Dess Martin periodinane-mediated cascade cyclization: generality, scope, and mechanism of the reaction, J. Am. Chem. Soc. 124 (2002) 2212-2220.
16. [16]
  [16] M.S. Yusubov, L.A. Drygunova, V.V. Zhdankin, 4,4-Bis(dichloroiodo)biphenyl and 3-(dichloroiodo)benzoic acid: new recyclable hypervalent iodine reagents for vicinal halomethoxylation of unsaturated compounds, Synthesis (2004) 2289-2292.
17. [17]
  [17] V.G. Shukla, P.D. Salgaonkar, K.G. Akamanchi, Molecular-iodine-catalyzed onepot synthesis of 1,5-benzodiazepine derivatives under solvent-free conditions, Synlett (2005) 1337-1339.
18. [18]
  [18] K.S. Feldman, D.B. Vidulova, Use of Stang's reagent, PhI(CN)OTf, to promote Pummerer-like oxidative cyclization of 2-(phenylthio)indoles, Tetrahedron Lett. 45 (2004) 5035-5037.
19. [19]
  [19] M.W. Justik, G.F. Koser, Oxidative rearrangements of arylalkenes with [hydroxy(tosyloxy)iodo]benzene in 95% methanol: a general, regiospecific synthesis of a-aryl ketones, Tetrahedron Lett. 45 (2004) 6159-6163.
20. [20]
  [20] L. Saikia, M. Rajesh, D. Srinivas, et al., Regiospecific oxyhalogenation of aromatics over SBA-15-supported nanoparticle group IV-VI metal oxides, Catal. Lett. 137 (2010) 190-201.
21. [21]
  [21] D.C. Crans, J.J. Smee, E. Gaidamauskas, et al., The chemistry and biochemistry of vanadium and the biological activities exerted by vanadium compounds, Chem. Rev. 104 (2004) 849-902.
22. [22]
  [22] A. Butler, J.N. Carter-Franklin, The role of vanadium bromoperoxidase in the biosynthesis of halogenated marine natural products, Nat. Prod. Rep. 21 (2004) 180-188.
23. [23]
  [23] P.D. Nightingale, G. Malin, P.S. Liss, Production of chloroform and other lowmolecular-weight halocarbons by some species of macroalgae, Limnol. Oceanogr. 40 (1995) 680-689.
24. [24]
  [24] G.A. Molander, O.A. Argintaru, I. Aron, et al., Nickel-catalyzed cross-coupling of potassium aryl and heteroaryltrifluoroborates with unactivated alkyl halides, Org. Lett. 12 (2010) 5783-5785.
25. [25]
  [25] G.A. Molander, I. Shin, L. Jean-Gerard, Palladium-catalyzed Suzuki Miyaura cross-coupling reactions of enantiomerically enriched potassium b-trifluoroboratoamides with various aryl- and hetaryl chlorides, Org. Lett. 12 (2010) 4384-4387.
26. [26]
  [26] S.D. Dreher, S.E. Lim, D.L. Sandrock, et al., Suzuki Miyaura cross-coupling reactions of primary alkyltrifluoroborates with aryl chlorides, J. Org. Chem. 74 (2009) 3626-3631.
27. [27]
  [27] Y. Kuwahara, A. Zhang, H. Soma, et al., Photochemical molecular storage of Cl2, HCl, and COCl2: synthesis of organochlorine compounds, salts, ureas, and polycarbonate with photodecomposed chloroform, Org. Lett. 14 (2012) 3376-3379.
28. [28]
  [28] Z.S. Zhou, X.H. He, An efficient and regioselective monobromination of electronrich aromatic compounds using catalytic hypervalent iodine(Ⅲ) reagent, Synthesis (2011) 207-209.
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1.
沈阳化工大学材料科学与工程学院沈阳 110142