CuI-nanoparticles-catalyzed selective synthesis of phenols, anilines, and thiophenols from aryl halides in aqueous solution

Journal of Organic Chemistry

Volumn 76, Issue 7, 2011, Pages 2296-2300

  Xu, Hua Jian ^a,b   Liang, Yu Feng ^a   Cai, Zhen Ya ^a   Qi, Hong Xia ^a   Yang, Chun Yan ^a   Feng, Yi Si ^a,b  

^a HEFEI UNIVERSITY OF TECHNOLOGY   (China)

^b Anhui Key Laboratory of Controllable Chemistry Reaction and Material Chemical Engineering   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS SOLUTIONS; ARYL HALIDES; SELECTIVE SYNTHESIS; SUBSEQUENT REDUCTION; SULFUR POWDERS; THIOPHENOLS;

ANILINE; CATALYSIS; CHELATION; HYDROXYLATION; METAL HALIDES; NANOPARTICLES; ORGANIC SOLVENTS; SULFUR;

PHENOLS;

AMMONIA; ANILINE; CUI NANOPARTICLE; HALIDE; NANOPARTICLE; PHENOL; SULFUR; THIOPHENOL; UNCLASSIFIED DRUG;

AMINATION; AQUEOUS SOLUTION; ARTICLE; CATALYSIS; HYDROXYLATION; SYNTHESIS;

ANILINE COMPOUNDS; CATALYSIS; COPPER; HYDROCARBONS, HALOGENATED; IODIDES; LIGANDS; MOLECULAR STRUCTURE; NANOPARTICLES; PHENOLS; SOLUTIONS; SOLVENTS; SULFHYDRYL COMPOUNDS;

EID: 79953189669     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102506x     Document Type: Article

References (69)

1. For phenols: Tyman, J. H. P. Synthetic and Natural Phenols; Elsevier: New York, 1996.
2. Rappoport, Z. The Chemistry of Phenols; Wiley-VCH: Weinheim, Germany, 2003.
3. For anilines: Weissermel, K.; Arpe, H. J. Industry Organic Chemistry; Wiley-VCH: Weinheim, Germany, 1997
4. Lawrence, S. A. Amines: Synthesis Properties and Application; Cambridge University Press: Cambridge, UK, 2004.
5. For thiophenols: Thuillier, A.; Metzner, P. Sulfur Reagents in Organic Synthesis; Academic Press: New York, 1994.
6. Anastas, P.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: Oxford, UK, 1998.
7. Willis, M. C. Angew. Chem., Int. Ed. 2007, 46, 3402
8. Anderson, K. W.; Ikawa, T.; Tundel, R. E.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 10694
9. Sergeev, A. G.; Schulz, T.; Torborg, C.; Spannenberg, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 7595
10. Schulz, T.; Torborg, C.; Schäffner, B.; Huang, J.; Zapf, A.; Kadyrov, R.; Börner, A.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 918
11. Gallon, B. J.; Kojima, R. W.; Kaner, R. B.; Diaconescu, P. L. Angew. Chem., Int. Ed. 2007, 46, 7251
12. Chen, G. S.; Chan, A. S. C.; Kwong, F. Y. Tetrahedron Lett. 2007, 48, 473
13. Dumrath, A.; Wu, X. F.; Neumann, H.; Spannenberg, A.; Jackstell, R.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 8988
14. Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 10028
15. Surry, D. S.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 10354
16. Schulz, T.; Torborg, C.; Enthaler, S.; Schäffner, B.; Dumrath, A.; Spannenberg, A.; Neumann, H.; Börner, A.; Beller, M. Chem.-Eur. J. 2009, 15, 4528
17. Vo, G. D.; Hartwig, J. F. J. Am. Chem. Soc. 2009, 131, 11049
18. Lundgren, R. J.; Peters, B. D.; Alsabeh, P. G.; Stradiotto, M. Angew. Chem., Int. Ed. 2010, 49, 4071
19. Lee, D. Y.; Hartwig, J. F. Org. Lett. 2005, 6, 1169
20. Yi, J.; Fu, Y.; Xiao, B.; Cui, W. C.; Guo, Q. X. Tetrahedron Lett. 2011, 52, 205
21. Kormos, C. M.; Leadbeater, N. E. Tetrahedron 2006, 62, 4728
22. Zhao, D. B.; Wu, N. J.; Zhang, S.; Xi, P. H.; Su, X. Y.; Lan, J. B.; You, J. S. Angew. Chem., Int. Ed. 2009, 48, 8729
23. Tlili, A.; Xia, N.; Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 8725
24. Ren, Y. L.; Cheng, L.; Tian, X. Z.; Zhao, S.; Wang, J. J.; Hou, C. D. Tetrahedron Lett. 2010, 51, 43
25. Maurer, S.; Liu, W.; Zhang, X.; Jiang, Y.; Ma, D. Synlett 2010, 976
26. Yang, D.; Fu, H. Chem.-Eur. J. 2010, 16, 2366
27. Jing, L.; Wei, J.; Zhou, L.; Huang, Z.; Li, Z.; Zhou, X. Chem. Commun. 2010, 4767
28. Wu, Z.; Jiang, Z.; Wu, D.; Xiang, H.; Zhou, X. Eur. J. Org. Chem. 2010, 1854
29. Meng, F.; Zhu, X.; Li, Y.; Xie, J.; Wang, B.; Yao, J.; Wan, Y. Eur. J. Org. Chem. 2010, 6149
30. Xu, H.; Wolf, C. Chem. Commun. 2009, 3035
31. Jiang, L.; Lu, X.; Zhang, H.; Jiang, Y.; Ma, D. J. Org. Chem. 2009, 74, 4542
32. Wang, D.; Cai, Q.; Ding, K. Adv. Synth. Catal. 2009, 351, 1722
33. Guo, Z.; Guo, J.; Song, Y.; Wang, L.; Zou, G. Appl. Organomet. Chem. 2009, 23, 150
34. Xia, N.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 337
35. Kim, J.; Chang, S. Chem. Commun. 2008, 3052
36. Elmkaddem, M. K.; Fischmeister, C.; Thomas, C. M.; Renaud, J. L. Chem. Commun. 2010, 925
37. Ntaganda, R.; Dhudshia, B.; Macdonald, C. L. B.; Thadani, A. N. Chem. Commun. 2008, 6200
38. Anderson, C. A.; Taylor, P. G.; Zeller, M. A.; Zimmerman, S. C. J. Org. Chem. 2010, 75, 4848
39. Wu, X. F.; Darcel, C. Eur. J. Org. Chem. 2009, 4753
40. Gao, X.; Fu, H.; Qiao, R.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2008, 73, 6864
41. Tao, C. Z.; Li, J.; Fu, Y.; Liu, L.; Guo, Q. X. Tetrahedron Lett. 2008, 49, 70
42. Markiewicz, J. T.; Wiest, O.; Helquist, P. J. Org. Chem. 2010, 75, 4887
43. Yang, C. T.; Fu, Y.; Huang, Y. B.; Yi, J.; Guo, Q. X.; Liu, L. Angew. Chem., Int. Ed. 2009, 48, 7398
44. Tao, C. Z.; Liu, W. W.; Lv, A. F.; Sun, M. M.; Tian, Y.; Wang, Q.; Zhao, J. Synlett 2010, 1355
45. Jiang, Y.; Qin, Y.; Xie, S.; Zhang, X.; Dong, J.; Ma, D. Org. Lett. 2009, 11, 5250
46. Grieco, P. A. Organic Synthesis in Water; Blackie A & P: London, UK, 1998.
47. Li, C. J. Chem. Rev. 2005, 105, 3095
48. Blackmond, D. G.; Armstrong, A.; Coomber, V.; Wells, A. Angew. Chem., Int. Ed. 2007, 46, 3798
49. Minakata, S.; Komatsu, M. Chem. Rev. 2009, 109, 711
50. Sheldon, R. A. Green Chem. 2005, 7, 267
51. Li, C. J.; Trost, B. M. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 13197
52. Astruc, D.; Lu, F.; Aranzaes, J. R. Angew. Chem., Int. Ed. 2005, 44, 7852
53. Thathagar, M. B.; Beckers, J.; Rothenberg, G. J. Am. Chem. Soc. 2002, 124, 11858
54. Thathagar, M. B.; Beckers, J.; Rothenberg, G. Green Chem. 2004, 6, 215
55. Rout, L.; Sen, T. K.; Punniyamurthy, T. Angew. Chem., Int. Ed. 2007, 46, 5583
56. Rout, L.; Jammi, S.; Punniyamurthy, T. Org. Lett. 2007, 9, 3397
57. Jammi, S.; Sakthivel, S.; Rout, L.; Mukherjee, T.; Mondal, S.; Mitra, R.; Saha, P.; Punniyamurthy, T. J. Org. Chem. 2009, 74, 1971
58. Sreedhar, B.; Arundhathi, R.; Reddy, P. L.; Kantam, M. L. J. Org. Chem. 2009, 74, 7951
59. The preparation method of CuI nanoparticles was inspired by the work of Qian's group on preparation of CuI nanorods: Li, X. L.; Zhu, X. Y.; Duan, T. L.; Qian, Y. T. Solid State Commun. 2006, 138, 526
60. For selected examples of chemoselective N- or O-arylation reactions: Shafir, A.; Lichtor, P. A.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3490
61. Job, G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 3703
62. Maiti, D.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 17423
63. 3 solution afforded 17% conversion and 11% yield under the present system for 72 h. No further attempts to optimize this reaction have been made. For detailed explanation of the reactivity of aryl chlorides, see: Mukhopadhyay, S.; Rothenberg, G.; Sasson, Y. Adv. Synth. Catal. 2001, 343, 274
64. The reaction proceeded smoothly at 40 °C to give aryl disulfides exclusively, which underwent reductive cleavage when treated with zinc dust and diluted hydrochloric acid to yield the thiophenols.
65. Zavitz, K. Patent PCT Int. Appl. WO 2004091522, 2004.
66. Matsuki, Y.; Dan, J.; Fukuhara, K.; Ito, T.; Nambara, T. Chem. Pharm. Bull. 1988, 36, 1431
67. Leaching study proved that it is intrinsically heterogeneous, see the Supporting Information. For leaching studies of metal nanoparticles, see: Gaikwad, A. V.; Holuigue, A.; Thathagar, M. B.; ten Elshof, J. E.; Rothenberg, G. Chem.-Eur. J. 2007, 13, 6908
68. Pachón, L. D.; Rothenberg, G. Appl. Organomet. Chem. 2008, 22, 288
69. Tentative proposals on the mechanism of hydroxylation about ion exchange were figured out, please see Scheme S1-S3 in the Supporting Information.