Catalytic acceptorless dehydrogenative coupling of arylhydrazines and alcohols for the synthesis of arylhydrazones

Journal of Organic Chemistry

Volumn 79, Issue 17, 2014, Pages 8031-8039

  Li, Feng ^a   Sun, Chunlou ^a   Wang, Nana ^a  

^a NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC COMPOUNDS;

ARYLHYDRAZINES; DEHYDROGENATIVE COUPLING; DIRECT SYNTHESIS;

BYPRODUCTS;

ALCOHOL DERIVATIVE; ARYLHYDRAZINE DERIVATIVE; ARYLHYDRAZONE DERIVATIVE; HYDRAZINE DERIVATIVE; HYDRAZONE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; DEHYDROGENATION; HYDROGENATION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; STEREOSPECIFICITY; SYNTHESIS;

EID: 84910009136     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501161u     Document Type: Article

References (74)

1. Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875-2911
2. Knolker, H. J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303-4427
3. Schmidt, A. W.; Reddy, K. R.; Knolker, H. J. Chem. Rev. 2012, 112, 3193-3328
4. Fustero, S.; Sanchez-Rosello, M.; Barrio, P.; Simon-Fuentes, A. Chem. Rev. 2011, 111, 6984-7034
5. Lebedev, A. Y.; Khartulyari, A. S.; Voskoboynikov, A. Z. J. Org. Chem. 2005, 70, 596-602
6. Vina, D.; Olmo, E.; López-Pérez, J. L.; Feliciano, A. S. Org. Lett. 2007, 9, 525-528
7. Muller, S.; List, B. Angew. Chem., Int. Ed. 2009, 48, 9975-9978
8. Thiel, O. R.; Achmatowicz, M. M.; Reichelt, A.; Larsen, R. D. Angew. Chem., Int. Ed. 2010, 49, 8395-8398
9. Hernández, S.; Moreno, I.; SanMartin, R.; Gómez, G.; Herrero, M. T.; Domínguez, E. J. Org. Chem. 2010, 75, 434-441
10. Guru, M. M.; Ali, M. A.; Punniyamurthy, T. J. Org. Chem. 2011, 76, 5295-5308
11. Aljaar, N.; Conrad, J.; Beifuss, U. J. Org. Chem. 2013, 78, 1045-1053
12. Duan, X. Y.; Yang, X. L.; Fang, R.; Peng, X. X.; Yu, W.; Han, B. J. Org. Chem. 2013, 78, 10692-10704
13. Martinez, A.; Webber, M. J.; Muller, S.; List, B. Angew. Chem., Int. Ed. 2013, 52, 9486-9490
14. Dabideen, D. R.; Cheng, K. F.; Aljabari, B.; Miller, E. J.; Pavlov, V. A.; Al-Abed, Y. J. Med. Chem. 2007, 50, 1993-1997
15. Baliani, A.; Bueno, G. J.; Stewart, M. L.; Yardley, V.; Brun, R.; Barrett, M. P.; Gilbert, I. H. J. Med. Chem. 2005, 48, 5570-5579
16. Chimenti, F.; Maccioni, E.; Secci, D.; Bolasco, A.; Chimenti, P.; Granese, A.; Befani, O.; Turini, P.; Alcaro, S.; Ortuso, F.; Cardia, M. C.; Distinto, S. J. Med. Chem. 2007, 50, 707-712
17. Lawrence, H. R.; Pireddu, R.; Chen, L.; Luo, Y.; Sung, S. S.; Szymanski, A. M.; Yip, M. L. R.; Guida, W. C.; Sebti, S. M.; Wu, J.; Lawrence, N. J. J. Med. Chem. 2008, 51, 4948-4956
18. Fattorusso, C.; Campiani, G.; Kukreja, G.; Persico, M.; Butini, S.; Romano, M. P.; Altarelli, M.; Ros, S.; Brindisi, M.; Savini, L.; Novellino, E.; Nacci, V.; Fattorusso, E.; Parapini, S.; Basilico, N.; Taramelli, D.; Yardley, V.; Croft, S.; Borriello, M.; Gemma, S. J. Med. Chem. 2008, 51, 1333-1343
19. Downing, R. S.; Kunkeler, P. J. The Fischer Indole Synthesis. In Fine Chemicals through Heterogeneous Catalysis, 1st ed.; Sheldon, R. A.; van Bekkum, H., Eds.; Wiley-VCH Verlag GmbH: Weinheim, Germany, 2001; pp 178-179.
20. Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6621-6622
21. Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10215-10263
22. Thiel, O. R.; Achmatowicz, M. M.; Reichelt, A.; Larsen, R. D. Angew. Chem., Int. Ed. 2010, 49, 8395-8398
23. Gnanaprakasam, B.; Zhang, J.; Milstein, D. Angew. Chem., Int. Ed. 2010, 49, 1468-1471
24. Maggi, A.; Madsen, R. Organometallics 2012, 31, 451-455
25. Nakajima, Y.; Okamoto, Y.; Chang, Y. H.; Ozawa, F. Organometallics 2013, 32, 2918-2925
26. Musa, S.; Fronton, S.; Vaccaro, L.; Gelman, D. Organometallics 2013, 32, 3069-3073
27. Esteruelas, M. A.; Honczek, N.; Olivan, M.; Onate, E.; Valencia, M. Organometallics 2011, 30, 2468-2471
28. Zhang, G.; Hanson, S. K. Org. Lett. 2013, 15, 650-653
29. For a recent review about acceptorless dehydrogenative and related transformations in chemical synthesis, see: Gnanaprakasam, B.; Milstein, D. Science 2013, 341, 1229712
30. Hamid, M. H. S. A.; Slatford, P. A.; Williams, J. M. J. Adv. Synth. Catal. 2007, 349, 1555-1575
31. Nixon, T. D.; Whittlesey, M. K.; Williams, J. M. J. Dalton Trans. 2009, 753-765
32. Dobereiner, G. E.; Grabtree, R. H. Chem. Rev. 2010, 110, 681-703
33. Guillena, G.; Ramon, D.; Yus, M. Chem. Rev. 2010, 110, 1611-1641
34. Suzuki, T. Chem. Rev. 2011, 111, 1825-1845
35. Bahn, S.; Imm, S.; Neubert, L.; Zhang, M.; Neumann, H.; Beller, M. ChemCatChem 2011, 3, 1853-1864
36. Marr, A. C. Catal. Sci. Technol. 2012, 2, 279-287
37. Pan, S.; Shibata, T. ACS Catal. 2013, 3, 704-712
38. Porcheddu and co-workers demonstrated the synthesis of indoles via tandem Ru-catalyzed hydrogen-transfer/Fischer cyclization from arylhydrazines and alcohols. However, the stoichiometric amount of crotonitrile is required as a hydrogen acceptor for the generation of arylhydrazones (intermediates); see: Porcheddu, A.; Mura, M. G.; Luca, L. D.; Pizzetti, M.; Taddei, M. Org. Lett. 2012, 14, 6112-6115
39. Li, F.; Shan, H.; Kang, Q.; Chen, L. Chem. Commun. 2011, 47, 5058-5060
40. Li, F.; Shan, H.; Chen, L.; Kang, Q.; Zou, P. Chem. Commun. 2012, 48, 603-605
41. Li, F.; Kang, Q.; Shan, H.; Chen, L.; Xie, J. Eur. J. Org. Chem. 2012, 5085-5092
42. Li, F.; Xie, J.; Shan, H.; Sun, C.; Chen, L. RSC Adv. 2012, 2, 8645-8652
43. Li, F.; Chen, L.; Kang, Q.; Cai, J.; Zhu, G. New J. Chem. 2013, 37, 624-631
44. Li, F.; Sun, C.; Shan, H.; Zou, X.; Xie, J. ChemCatChem 2013, 5, 1543-1552
45. Li, F.; Qu, P.; Ma, J.; Zou, X.; Sun, C. ChemCatChem 2013, 5, 2178-2182
46. Sun, C.; Zou, X.; Li, F. Chem.-Eur. J. 2013, 19, 14030-14033
47. Qu, P.; Sun, C.; Ma, J.; Li, F. Adv. Synth. Catal. 2014, 356, 447-459
48. Fujita, K.; Yamamoto, K.; Yamaguchi, R. Org. Lett. 2002, 4, 2691-2694
49. Fujita, K.; Li, Z.; Ozeki, N.; Yamaguchi, R. Tetrahedron Lett. 2003, 44, 2687-2690
50. Fujita, K.; Fujii, T.; Yamaguchi, R. Org. Lett. 2004, 6, 3525-3528
51. Fujita, K.; Enoki, Y.; Yamaguchi, R. Tetrahedron 2008, 64, 1943-1954
52. Yamaguchi, R.; Kawagoe, S.; Asai, C.; Fujita, K. Org. Lett. 2008, 10, 181-184
53. Fujita, K.; Komatsubara, A.; Yamaguchi, R. Tetrahedron 2009, 65, 3624-3628
54. Zhu, M.; Fujita, K.; Yamaguchi, R. Org. Lett. 2010, 12, 1336-1339
55. Robinson, B. The Fischer Indole Synthesis; John Wiley and Sons: Chichester, U.K., 1982.
56. Smith, P. A. S. Derivatives of Hydrazine and Other Hydronitrogens Having N-N Bonds, 2nd ed.; The Benjamin/Cummings Publishing Co.: Reading, MA, 1983.
57. Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6621-6622
58. Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251-10263
59. 2 toward the oxidation of alcohols to the corresponding aldehydes; see: Fujita, K.; Furukawa, S.; Yamaguchi, R. J. Organomet. Chem. 2002, 649, 289-292
60. Siddiqui, A. A.; Khan, N. H.; Ali, M.; Kidwai, A. R. Synth. Commun. 1977, 7, 71-78
61. Zey, R. L.; Richter, G.; Randa, H. J. Heterocyclic Chem. 1989, 26, 1437-1439
62. Dalla-Vechia, L.; Reichart, B.; Glasnov, T.; Miranda, L. S. M.; Kappe, C. O.; de Souza, R. O. M. A. Org. Biomol. Chem. 2013, 11, 6806-6813
63. Lerch, U.; Konig, J. Synthesis 1983, 157-158
64. Leung, D.; Anslyn, E. V. Org. Lett. 2011, 13, 2298-2301
65. Kang, J. W.; Maitlis, P. M. J. Am. Chem. Soc. 1968, 90, 3259-3261
66. Kang, J. W.; Maitlis, P. M.; Moseley, K. J. Am. Chem. Soc. 1969, 91, 5970-5977
67. Owston, N. A.; Parker, A. J.; Williams, J. M. J. Org. Lett. 2007, 9, 73-75
68. Dubrovskiy, A. V.; Larock, R. C. J. Org. Chem. 2012, 77, 11232-11256
69. Fusco, R.; Sannicolb, F. J. Org. Chem. 1984, 49, 4374-4378
70. Asiri, A. M.; Ismail, I. M. I.; Al-Amry, K. A.; Fatani, N. A. Dyes Pigm. 2005, 67, 111-115
71. Mino, T.; Shirae, Y.; Sakamoto, M.; Fujita, T. J. Org. Chem. 2005, 70, 2191-2194
72. Zhang, G.; Miao, J. M.; Zhao, Y.; Ge, H. B. Angew. Chem., Int. Ed. 2012, 51, 8318-8321
73. Lundgren, R. J.; Stradiotto, M. Angew. Chem., Int. Ed. 2010, 49, 8686-8690
74. Wu, J.; Talwar, D.; Johnston, S.; Yan, M.; Xiao, J. Angew. Chem., Int. Ed. 2013, 52, 6983-6987