Preparation of unsymmetrical ketones from tosylhydrazones and aromatic aldehydes via formyl C-H bond insertion

Organic Letters

Volumn 16, Issue 11, 2014, Pages 3064-3067

  Allwood, Daniel M ^a   Blakemore, David C ^b   Ley, Steven V ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AZO COMPOUND; HYDRAZONE DERIVATIVE; KETONE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; SYNTHESIS;

ALDEHYDES; AZO COMPOUNDS; CATALYSIS; HYDRAZONES; HYDROGEN BONDING; KETONES; MOLECULAR STRUCTURE;

EID: 84902083696     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol5011714     Document Type: Article

References (51)

1. Smith, M. B.; March, J. In March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 5 th ed.; John Wiley & Sons: New York, 2001.
2. Kürti, L.; Czakó, B. In Strategic Applications of Named Reactions in Organic Synthesis; Elsevier Academic Press: Burlington, 2005.
3. Li, J.; Zhang, X.; Zhang, Z.; Padakanti, P. K.; Jin, H.; Cui, J.; Li, A.; Zeng, D.; Rath, N. P.; Flores, H.; Perlmutter, J. S.; Parsons, S. M.; Tu, Z. J. Med. Chem. 2013, 56, 6216-6233
4. Uto, Y.; Ogata, T.; Yohei, K.; Ueno, Y.; Miyazawa, Y.; Kurata, H.; Deguchi, T.; Watanabe, N.; Konishi, M.; Okuyama, R.; Kurikawa, N.; Takagi, T.; Wakimoto, S.; Ohsumi, J. Bioorg. Med. Chem. Lett. 2010, 20, 341-345
5. For a review on the preparation and stability of alkyl organometallics, see: Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417-1492
6. Mock, W. L.; Hartman, M. E. J. Org. Chem. 1977, 42, 459-465
7. Hashimoto, N.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1980, 21, 4619-4622
8. Nagao, K.; Chiba, M.; Kim, S.-W. Synthesis 1983, 197-199
9. Maruoka, K.; Concepcion, A. B.; Yamamoto, H. J. Org. Chem. 1994, 59, 4725-4726
10. Hashimoto, T.; Naganawa, Y.; Maruoka, K. J. Am. Chem. Soc. 2008, 130, 2434-2435
11. Morandi, B.; Carreira, E. M. Angew. Chem., Int. Ed. 2011, 50, 9085-9088
12. Gao, L.; Kang, B. C.; Ryu, D. H. J. Am. Chem. Soc. 2013, 135, 14556-14559
13. Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Synthesis 1994, 1283-1290
14. Kanemasa, S.; Kanai, T.; Araki, T.; Wada, E. Tetrahedron Lett. 1999, 40, 5055-5058
15. Dudley, M. E.; Morshed, Md. M.; Brennan, C. L.; Islam, M. S.; Ahmad, M. S.; Atuu, M.-R.; Branstetter, B.; Hossain, M. M. J. Org. Chem. 2004, 69, 7599-7608
16. Zhang, Y.; Wang, J. Chem. Commun. 2009, 5350-5361
17. Fructos, M. R.; Díaz-Requejo, M. M.; Pérez, P. J. Chem. Commun. 2009, 5153-5155
18. Aoyama, T.; Shioiri, T. Synthesis 1988, 228-229
19. López-Herrera, F. J.; Valpuesta-Fernández, M.; García-Claros, S. Tetrahedron 1990, 46, 7165-7174
20. Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Synlett 1994, 521-523
21. Sudrik, S. G.; Balaji, B. S.; Singh, A. P.; Mitra, R. B.; Sonawane, H. R. Synlett 1996, 369-370
22. Werner, R. M.; Shokek, O.; Davis, J. T. J. Org. Chem. 1997, 62, 8243-8346
23. Balaji, B. S.; Chanda, B. M. Tetrahedron 1998, 54, 13237-13252
24. Mahmood, S. J.; Saha, A. K.; Hossain, M. M. Tetrahedron 1998, 54, 349-358
25. Phukan, P.; Mohan, J. M.; Sudalai, A. J. Chem. Soc., Perkin Trans. 1 1999, 3685-3689
26. Bandgar, B. P.; Pandit, S. S.; Sadavarte, V. S. Green Chem. 2001, 3, 247-249
27. Yadav, J. S.; Subba Reddy, B. V.; Eeshwaraiah, B.; Reddy, P. N. Tetrahedron 2005, 61, 875-878
28. Wu, M.; Sun, Q.; Yang, C.; Chen, D.; Ding, J.; Chen, Y.; Lin, L.; Xie, Y. Bioorg. Med. Chem. Lett. 2007, 17, 869-873
29. Murata, H.; Ishitani, H.; Iwamoto, M. Tetrahedron Lett. 2008, 49, 4788-4791
30. Yadav, J. S.; Subba Reddy, B. V.; Purnima, K. V.; Jhansi, S.; Nagaiah, K.; Lingaiah, N. Catal. Commun. 2008, 9, 2361-2364
31. Jeyakumar, K.; Chand, D. K. Synthesis 2008, 1685-1687
32. Hashimoto, T.; Miyamoto, H.; Naganawa, Y.; Maruoka, K. J. Am. Chem. Soc. 2009, 131, 11280-11281
33. Bartrum, H. E.; Blakemore, D. C.; Moody, C. J.; Hayes, C. J. J. Org. Chem. 2010, 75, 8674-8676
34. Bandyopadhyay, A.; Agrawal, N.; Mali, S. M.; Jadhav, S. V.; Gopi, H. N. Org. Biomol. Chem. 2010, 8, 4855-4860
35. Li, W.; Wang, J.; Hu, X.; Shen, K.; Wang, W.; Chu, Y.; Lin, L.; Liu, X.; Feng, X. J. Am. Chem. Soc. 2010, 132, 8532-8533
36. Gao, L.; Kang, B. C.; Hwang, G.-S.; Ryu, D. H. Angew. Chem., Int. Ed. 2012, 51, 8322-8325
37. Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O. Eur. J. Org. Chem. 2002, 1562-1565
38. Zhu, Z.; Espenson, J. H. J. Org. Chem. 1995, 60, 7090-7091
39. Aggarwal, V. K.; Abdel-Rahman, H.; Jones, R. V. H.; Lee, H. Y.; Reid, B. D. J. Am. Chem. Soc. 1994, 116, 5973-5974
40. Mahmood, S. J.; Hossain, M. M. J. Org. Chem. 1998, 63, 3333-3336
41. Holmquist, C. R.; Roskamp, E. J. J. Org. Chem. 1989, 54, 3258-3260
42. Holmquist, C. R.; Roskamp, E. J. Tetrahedron Lett. 1992, 33, 1131-1134
43. Padwa, A.; Hornbuckle, S. F.; Zhang, Z.; Zhi, L. J. Org. Chem. 1990, 55, 5297-5299
44. Nomura, K.; Iida, T.; Hori, K.; Yoshii, E. J. Org. Chem. 1994, 59, 488-490
45. Loeschorn, C. A.; Nakajima, M.; McCloskey, P. J.; Anselme, P. J. J. Org. Chem. 1983, 48, 4407-4410
46. Wommack, A. J.; Moebius, D. C.; Travis, A. L.; Kingsbury, J. S. Org. Lett. 2009, 11, 3202-3205
47. Angle, S. R.; Neitzel, M. L. J. Org. Chem. 2000, 65, 6458-6461
48. Aggarwal, V. K.; de Vicente, J.; Pelotier, B.; Holmes, I. P.; Bonnert, R. V. Tetrahedron Lett. 2000, 41, 10327-10331
49. Bradley, J. N.; Cowell, G. W.; Ledwith, A. J. Chem. Soc. 1964, 4334-4339
50. Wulfman, D. S.; Linstrumelle, G.; Cooper, C. F. In The Chemistry of Diazonium and Diazo Groups; Patai, S., Ed.; Interscience: New York, 1978.
51. Allwood, D. M.; Blakemore, D. C.; Brown, A. D.; Ley, S. V. J. Org. Chem. 2014, 79, 328-338