Synthesis of ortho/ortho ′-substituted 1,1-diarylethylenes through cross-coupling reactions of sterically encumbered hydrazones and aryl halides

Journal of Organic Chemistry

Volumn 78, Issue 2, 2013, Pages 445-454

  Roche, Maxime ^a   Hamze, Abdallah ^a   Provot, Olivier ^a   Brion, Jean Daniel ^a   Alami, Mouad ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC RINGS; ARYL HALIDES; BROAD SPECTRUM; CROSS COUPLING REACTIONS; HYDRAZONES; REACTION CONDITIONS; SEALED TUBES;

BENZENE;

METAL HALIDES;

HALIDE; HYDRAZONE DERIVATIVE; LIGAND; N TOSYLHYDRAZONE DERIVATIVE; PALLADIUM; SOLVENT; UNCLASSIFIED DRUG; XANTHENE DERIVATIVE;

ARTICLE; CROSS COUPLING REACTION;

CATALYSIS; CROSS-LINKING REAGENTS; ETHYLENES; HYDRAZONES; HYDROCARBONS, HALOGENATED; MOLECULAR STRUCTURE; XANTHENES;

EID: 84872580639     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3023268     Document Type: Article

References (51)

1. Trost, B. M. In Transition Metals for Organic Synthesis, 2 nd ed.; Wiley-VCH Verlag GmbH: Weinheim, 2008; p 2.
2. Bräse, S.; Meijere, A. D. In Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; Wiley-VCH Verlag GmbH: Weinheim, 2008; p 217.
3. Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780
4. Beller, M.; Zapf, A.; Riermeir, T. H. In Transition Metals for Organic Synthesis, 2 nd ed.; Beller, M.; Bolm, C., Eds.; Wiley-VCH Verlag GmbH: Weinheim, 2004; p 271. For C-H activation review, see
5. Godula, K.; Sames, D. Science 2006, 312, 67
6. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
7. Baudoin, O. Chem. Soc. Rev. 2011, 40, 4902
8. Messaoudi, S.; Brion, J.-D.; Alami, M. Eur. J. Org. Chem. 2010, 2010, 6495
9. Hamada, T.; Chieffi, A.; Åhman, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1261
10. Carter, D. S.; Van Vranken, D. L. Tetrahedron Lett. 1999, 40, 1617
11. Greenman, K. L.; Carter, D. S.; Van Vranken, D. L. Tetrahedron 2001, 57, 5219
12. Greenman, K. L.; Van Vranken, D. L. Tetrahedron 2005, 61, 6438
13. Devine, S. K. J.; Van Vranken, D. L. Org. Lett. 2007, 9, 2047
14. Kudirka, R.; Van Vranken, D. L. J. Org. Chem. 2008, 73, 3585
15. Kudirka, R.; Devine, S. K. J.; Adams, C. S.; Van Vranken, D. L. Angew. Chem., Int. Ed. 2009, 48, 3677
16. Fulton, J. R.; Aggarwal, V. K.; de Vicente, J. Eur. J. Org. Chem. 2005, 1479
17. Barluenga, J.; Valdés, C. Angew. Chem., Int. Ed. 2011, 50, 7486
18. Shao, Z.; Zhang, H. Chem. Soc. Rev. 2012, 41, 560
19. Barluenga, J.; Moriel, P.; Valdés, C.; Aznar, F. Angew. Chem., Int. Ed. 2007, 46, 5587
20. Barluenga, J.; Quiñones, N.; Cabal, M.-P.; Aznar, F.; Valdés, C. Angew. Chem., Int. Ed. 2011, 50, 2350
21. Barluenga, J.; Tomás-Gamasa, M.; Aznar, F.; Valdés, C. Chem.-Eur. J. 2010, 16, 12801
22. Barluenga, J.; Tomás-Gamasa, M.; Aznar, F.; Valdés, C. Adv. Synth. Catal. 2010, 352, 3235
23. Barluenga, J.; Tomas-Gamasa, M.; Moriel, P.; Amar, F.; Valdés, C. Chem.-Eur. J. 2008, 14, 4792
24. Treguier, B.; Hamze, A.; Provot, O.; Brion, J. D.; Alami, M. Tetrahedron Lett. 2009, 50, 6549
25. Barluenga, J.; Florentino, L.; Aznar, F.; Valdés, C. Org. Lett. 2010, 13, 510
26. Xiao, Q.; Ma, J.; Yang, Y.; Zhang, Y.; Wang, J. Org. Lett. 2009, 11, 4732
27. Xiao, Q.; Xia, Y.; Li, H.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2011, 50, 1114
28. Zhou, L.; Shi, Y.; Xiao, Q.; Liu, Y.; Ye, F.; Zhang, Y.; Wang, J. Org. Lett. 2011, 13, 968
29. Ye, F.; Ma, X.; Xiao, Q.; Li, H.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2012, 134, 5742
30. Hamze, A.; Treguier, B.; Brion, J.-D.; Alami, M. Org. Biomol. Chem. 2011, 9, 6200
31. Yao, T.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2012, 51, 775
32. Zhao, X.; Wu, G.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2011, 133, 3296
33. Zhao, X.; Jing, J.; Lu, K.; Zhang, Y.; Wang, J. Chem. Commun. 2010, 46, 1724
34. Zhou, F.; Ding, K.; Cai, Q. Chem.-Eur. J. 2011, 17, 12268
35. Hamze, A.; Brion, J.-D.; Alami, M. Org. Lett. 2012, 14, 2782
36. Hamze, A.; Veau, D.; Provot, O.; Brion, J. D.; Alami, M. J. Org. Chem. 2009, 74, 1337
37. Messaoudi, S.; Treguier, B.; Hamze, A.; Provot, O.; Peyrat, J. F.; De Losada, J. R.; Liu, J. M.; Bignon, J.; Wdzieczak-Bakala, J.; Thoret, S.; Dubois, J.; Brion, J. D.; Alami, M. J. Med. Chem. 2009, 52, 4538
38. Hamze, A.; Giraud, A.; Messaoudi, S.; Provot, O.; Peyrat, J. F.; Bignon, J.; Liu, J. M.; Wdzieczak-Bakala, J.; Thoret, S.; Dubois, J.; Brion, J. D.; Alami, M. ChemMedChem 2009, 4, 1912
39. Brachet, E.; Hamze, A.; Peyrat, J.-F.; Brion, J.-D.; Alami, M. Org. Lett. 2010, 12, 4042
40. Aziz, J.; Brachet, E.; Hamze, A.; Peyrat, J.-F.; Bernadat, G.; Morvan, E.; Bignon, J.; Wdzieczak-Bakala, J.; Desravines, D.; Dubois, J.; Tueni, M.; Yassine, A.; Brion, J.-D.; Alami, M. Org. Biomol. Chem. 2013, 11, 430
41. Rasolofonjatovo, E.; Tréguier, B.; Provot, O.; Hamze, A.; Brion, J.-D.; Alami, M. Eur. J. Org. Chem. 2012, 1603
42. Huang, Z.; Yang, Y.; Xiao, Q.; Zhang, Y.; Wang, J. Eur. J. Org. Chem. 2012, 6586-6593
43. Bamford, W. R.; Stevens, T. S. J. Chem. Soc. 1952, 4735
44. NaO- t -Bu was chosen as the optimal base for this coupling for two reasons: first, its cheap price compared to LiO- t -Bu, and second, because it was considered as a base often allowing the highest reaction rates and enabling the lowest catalyst loading for Pd-catalyzed reactions; see: Surry, D. S.; Buchwald, S. L. Chem. Sci. 2011, 2, 27
45. 50 = 930 mg/kg), see: https://msdsmanagement.msdsonline.com/MSDSonline/.
46. Gniadecki, R.; Assaf, C.; Bagot, M.; Dummer, R.; Duvic, M.; Knobler, R.; Ranki, A.; Schwandt, P.; Whittaker, S. Brit. J. Dermatol. 2007, 157, 433
47. Boehm, M. F.; Zhang, L.; Badea, B. A.; White, S. K.; Mais, D. E.; Berger, E.; Suto, C. M.; Goldman, M. E.; Heyman, R. A. J. Med. Chem. 1994, 37, 2930
48. Cong, Z.; Miki, T.; Urakawa, O.; Nishino, H. J. Org. Chem. 2009, 74, 3978
49. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals, 2 nd ed.; Pergamon Press: Oxford, 1980.
50. Creary, X.; Tam, W. W.; Albizati, K. F.; Stevens, R. V. Org. Synth. 1986, 64, 207
51. Mazza, S. M.; Lal, K.; Salomon, R. G. J. Org. Chem. 1988, 53, 3681