Transition-metal-free O-,S -, and N-arylation of alcohols, thiols, amides, amines, and related heterocycles

Journal of Organic Chemistry

Volumn 76, Issue 2, 2011, Pages 654-660

  Cano, Rafael ^a   Ramón, Diego J ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATIONS; BENZYNE; CARBOXAMIDES; HALOARENES; HETEROCYCLES; IN-SITU; N-ARYLATIONS; NEW PROTOCOL; PYRAZOLES; TRANSITION METAL CATALYSTS;

AMIDES; AMINES; BROMINE COMPOUNDS; CATALYSTS; CHEMICAL REACTIONS; DIMETHYL SULFOXIDE; PHENOLS; POTASSIUM; POTASSIUM HYDROXIDE; TRANSITION METALS;

REACTION INTERMEDIATES;

ALCOHOL DERIVATIVE; AMIDE; AMINE; ANILINE; AROMATIC COMPOUND; BROMIDE; DIMETHYL SULFOXIDE; HETEROCYCLIC AMINE; IMIDAZOLE DERIVATIVE; INDOLE DERIVATIVE; IODIDE; ISOTHIOCYANIC ACID DERIVATIVE; NUCLEOPHILE; PHENOL DERIVATIVE; POTASSIUM HYDROXIDE; PYRAZOLE DERIVATIVE; TRANSITION ELEMENT;

ARTICLE; ARYLATION; CATALYST; CHEMICAL STRUCTURE;

ALCOHOLS; AMIDES; AMINES; CATALYSIS; HETEROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SULFHYDRYL COMPOUNDS; TRANSITION ELEMENTS;

EID: 78651487650     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1022052     Document Type: Article

References (86)

1. Ullmann, F. Ber. Dtsch. Chem. Ges. 1903, 36, 2382-2384
2. For recent reviews, see: Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1469
3. Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400-5449
4. Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337-2364
5. Hartwig, J. F. Synlett 2006, 1283-1294
6. Corbet, J.-P.; Mignani, G. Chem. Rev. 2006, 106, 2651-2710
7. Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450-1460
8. Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534-1544
9. Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954-6971
10. Trost, B. M. Science 1991, 254, 1471-1477
11. Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T.; Williamson, T. C., Eds.; American Chemical Society: Washington, DC, 1996.
12. Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705
13. Sheldon, R. A.; Arends, I.; Hanefeld, U. Green Chemistry and Catalysis; Wiley-VCH: Weinheim, Germany, 2007.
14. Guillena, G.; Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2007, 46, 2358-2364
15. Guillena, G.; Ramón, D. J.; Yus, M. Chem. Rev. 2010, 110, 1611-1641
16. For recent representative examples, see: Correa, A.; Elmore, S.; Bolm, C. Chem.-Eur. J. 2008, 14, 3527-3529
17. Guo, D.; Huang, H.; Xu, J.; Jiang, H.; Liu, H. Org. Lett. 2008, 10, 4513-4516
18. Lee, H. W.; Chan, A. S. C.; Kwong, F. Y. Tetrahedron Lett. 2009, 50, 5868-5871
19. Swapna, K.; Kumar, A. V.; Reddy, V. P.; Rao, K. R. J. Org. Chem. 2009, 74, 7514-7517
20. For the catalytic role of contaminants, see: Buchwald, S. L.; Bolm, C. Angew. Chem., Int. Ed. 2009, 48, 5586-5587
21. Teo, Y.-C.; Chua, G.-L. Chem.-Eur. J. 2009, 15, 3072-3075
22. Chen, C.; Yang, L.-M. J. Org. Chem. 2007, 72, 6324-6327
23. Gao, C.-Y.; Yang, L.-M. J. Org. Chem. 2008, 73, 1624-1627
24. For recent representative examples see: Zhang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164-5173
25. Chouhan, G.; Wang, D.; Alper, H. Chem. Commun. 2007, 4809-4811
26. Zhu, X.; Su, L.; Huang, L.; Chen, G.; Wang, J.; Song, H.; Wan, Y. Eur. J. Org. Chem. 2009, 635-642
27. Zhu, L.; Li, G.; Guo, P.; Lan, J.; You, J. J. Org. Chem. 2009, 74, 2200-2202
28. Wu, X.-F.; Darcel, C. Eur. J. Org. Chem. 2009, 4753-4756
29. Sreedhar, B.; Arundhathi, R.; Reddy, P. L.; Kantam, M. L. J. Org. Chem. 2009, 74, 7951-7954
30. Diao, X.; Wang, Y.; Jiang, Y.; Ma, D. J. Org. Chem. 2009, 74, 7974-7954
31. Phillips, D. P.; Zhu, X.-F.; Lau, T. L.; He, X.; Yang, K.; Liu, H. Tetrahedron Lett. 2009, 50, 7293-7296
32. Alakonda, L.; Periasamy, M. J. Organomet. Chem. 2009, 694, 3859-3863
33. Jammi, S.; Krishnamoorthy, S.; Saha, P.; Kundu, D. S.; Sakthivel, S. Synlett 2009, 3323-3327
34. Haneda, S.; Adachi, Y.; Hayashi, M. Tetrahedron 2009, 65, 10459-10462
35. Hirano, K.; Biju, A. T.; Glorius, F. J. Org. Chem. 2009, 74, 9570-9572
36. Cai, Q.; Li, Z.; Wei, J.; Ha, C.; Pei, D.; Ding, K. Chem. Commun. 2009, 7581-7583
37. Guo, D.; Huang, H.; Zhou, Y.; Xu, J.; Jiang, H.; Chen, K.; Liu, H. Green Chem. 2010, 12, 276-281
38. Han, X. Tetrahedron Lett. 2010, 51, 360-362
39. Ali, M. A.; Punniyamurthy, T. Synthesis 2010, 908-910
40. For recent representative examples, see: Urgaonkar, S.; Xu, J.-H.; Verkade, J. G. J. Org. Chem. 2003, 68, 8416-8423
41. Rataboul, F.; Zapf, A.; Jackstell, R.; Harkal, S.; Riermeier, T.; Monsees, A.; Dingerdissen, U.; Beller, M. Chem.-Eur. J. 2004, 10, 2983-2990
42. Dai, Q.; Gao, W.; Liu, D.; Kapes, L. M.; Zhang, X. J. Org. Chem. 2006, 71, 3928-3934
43. Trabanco, A. A.; Vega, J. A.; Fernández, M. A. J. Org. Chem. 2007, 72, 8146-8148
44. Mantel, M. L. H.; lindhardt, A. T.; Lupp, D.; Skrydstrup, T. Chem.-Eur. J. 2010, 16, 5437-5442
45. For recent representative examples, see: Chang, J. W. W.; Chee, S.; Mak, S.; Buranaprasertsuk, P.; Chavasiri, W.; Chan, P. W. H. Tetrahedron Lett. 2007, 49, 2018-2022
46. Liu, X.; Fu, H.; Jiang, Y.; Zhao, Y. Synlett 2008, 221-224
47. Chen, W.; Li, J.; Fang, D.; Feng, C.; Zhang, C. Org. Lett. 2008, 10, 4565-4568
48. Jogdand, N. R.; Shingate, B. B.; Shingare, M. S. Tetrahedron Lett. 2009, 50, 4019-4021
49. Toumi, M.; Rincheval, V.; Young, A.; Gergeres, D.; Turos, E.; Couty, F.; Mignotte, B.; Evano, G. Eur. J. Org. Chem. 2009, 3368-3386
50. Cheng, L.; Liu, L.; Jia, H.; Wang, D.; Chen, Y.-J. J. Org. Chem. 2009, 74, 4650-4653
51. Cavalluzzi, M. M.; Bruno, C.; Lentini, G.; Lovece, A.; Catalano, A.; Carocci, A.; Franchini, C. Tetrahedron: Asymmetry 2009, 20, 1984-1991
52. Maiti, D.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 17423-17429
53. Maiti, D.; Buchwald, S. L. J. Org. Chem. 2010, 75, 1791-1794
54. For recent representative examples, see: Correa, A.; Carril, M.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 2880-2883
55. Fernández-Rodríguez, M. A.; Hartwig, J. F. J. Org. Chem. 2009, 74, 1663-1672
56. Fu, C.-F.; Liu, Y.-H.; Peng, S.-M.; Liu, S.-T. Tetrahedron 2010, 66, 2119-2122
57. Wang, H.; Jiang, L.; Chen, T.; Li, Y. Eur. J. Org. Chem. 2010, 2324-2329
58. Akkilagunta, V. K.; Reddy, V. P.; Rao, K. R. Synlett 2010, 1260-1264
59. Feng, Y.-S.; Li, Y.-Y.; Tang, L.; Wu, W.; Xu, H.-J. Tetrahedron Lett. 2010, 51, 2489-2492
60. Ma, D.; Geng, Q.; Zhang, H.; Jiang, Y. Angew. Chem., Int. Ed. 2010, 49, 1291-1294
61. For instance, see: Aelterman, W.; Lang, Y.; Willemsens, B.; Vervest, I.; Leurs, S.; De Knaep, F. Org. Process Res. Dev. 2001, 5, 467-471
62. Ding, Q.; He, X.; Wu, J. J. Comb. Chem. 2009, 11, 587-591
63. Pi, S.-S.; Zhang, X.-G.; Tang, R.-T.; Li, J.-H. Synlett 2009, 3032-3036
64. Shen, G.; Lv, X.; Bao, W. Eur. J. Org. Chem. 2009, 5897-5901
65. Bose, D. S.; Idrees, M. Synthesis 2010, 1983-1988
66. Ding, Q.; He, X.; Wu, J. J. Comb. Chem. 2009, 11, 587-591
67. For reviews on the use of arynes, see: Pellissier, H.; Santelli, M. Tetrahedron 2003, 59, 701-730
68. Peña, D.; Pérez, D.; Guitián, E. Angew. Chem., Int. Ed. 2006, 45, 3579-3581
69. Bunnett, J. F.; Hrutfiord, B. J. J. Am. Chem. Soc. 1961, 83, 1691-1697
70. Biehl, E. R.; Lapis, S.; Reeves, P. C. J. Org. Chem. 1974, 39, 1900-1902
71. Nakayama, J.; Yoshida, M.; Simamura, O. Bull. Chem. Soc. Jpn. 1975, 48, 2397-2398
72. Zoratti, M.; Bunnett, J. F. J. Org. Chem. 1980, 45, 1769-1776
73. Aliaga, M. J.; Ramón, D. J.; Yus, M. Org. Biomol. Chem. 2010, 8, 43-46
74. Cano, R.; Ramón, D. J.; Yus, M. J. Org. Chem. 2010, 75, 3458-3460
75. The DMSO/KOH mixture was catalogued as a superbase and was used, independently from our work, in the transition-metal-free preparation of cross-coupling products: Yuan, Y.; Thomé, I.; Kim, S. H.; Chen, D.; Beyer, A.; Bonnamour, J.; Zuidema, E.; Chang, S.; Bolm, C. Adv. Synth. Catal. 2010, 352, 2892-2898
76. For examples of microwave-assisted hetero Ullmann reaction, see: Chow, W. S.; Chan, T. H. Tetrahedron Lett. 2009, 50, 1286-1289
77. Rolfe, A.; Hanson, P. R. Tetrahedron Lett. 2009, 50, 6935-6937
78. Colacino, E.; Villebrum, L.; Martínez, J.; Lamaty, F. Tetrahedron 2010, 66, 3730-3735
79. For the unique example of amination of aryl chlorides using potassium tert -butoxide as base in toluene at 135 °C, see: Beller, M.; Breindl, C.; Riermeir, T. H.; Tillack, A. J. Org. Chem. 2001, 66, 1403-1412
80. Teo, Y. C.; Chua, G.-L. Chem.-Eur. J. 2009, 15, 3072-3075
81. Khan, M. A.; Polya, J. B. J. Chem. Soc. C 1970, 85-91
82. Koppang, R. J. Fluorine Chem. 1975, 5, 323-333
83. Gasparini, F.; Caglioti, L.; Misiti, D.; Palmieri, G.; Ballini, R. Tetrahedron 1982, 38, 3609-3613
84. Bahrami, K.; Khodaei, M. M.; Naali, F. J. Org. Chem. 2008, 73, 6835-6837
85. Deng, X.; McAllister, H.; Mani, N. S. J. Org. Chem. 2009, 74, 5742-5745
86. Qian, W.; Jin, E.; Bao, W.; Zhang, Y. J. Chem. Res. 2005, 613-616