Palladium-catalyzed direct arylation of aryl(azaaryl)methanes with aryl halides providing triarylmethanes

Organic Letters

Volumn 9, Issue 12, 2007, Pages 2373-2375

  Niwa, Takashi ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; HALOGENATED HYDROCARBON; METHANE; PALLADIUM;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKYLATION; CATALYSIS; HYDROCARBONS, HALOGENATED; METHANE; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM;

EID: 34250849614     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0708119     Document Type: Article

References (46)

1. (a) Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998.
2. (b) Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, P., Eds.; Wiley-VCH: Weinheim, 2004.
3. (c) Cross-Coupling Reactions. A Practical Guide; Miyaura, N., Ed.; Springer: Berlin, 2002.
4. (d) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; John Wiley & Sons: New York, 2002.
5. (a) Dyker, G., Ed. Handbook of C-H Transformations; Wiley-VCH: Weinheim, Germany, 2005.
6. (b) Godula, K.; Sames, D. Science 2006, 312, 67-72.
7. (c) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077-1101.
8. (d) Miura, M.; Nomura, M. Top. Curr. Chem. 2002, 219, 211-241.
9. (e) Satoh, T.; Miura, M. Chem. Lett. 2007, 36, 200-205.
10. (f) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174-238.
11. Direct ortho-arylation of phenols: (a) Satoh, T.; Inch, I.; Kawamura, Y.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 2239-2246.
12. (b) Cuny, G. D. Tetrahedron Lett. 2004, 45, 5167-5170 and refs cited therein.
13. Direct arylation of electron-rich arenes: Yanagisawa, S.; Sudo, T.; Noyori, R.; Itami, K. J. Am. Chem. Soc. 2006, 128, 11748-11749 and refs cited therein. Also note that a large part of ref 2 describes this type of transformation.
14. Direct arylation of electron-deficient arenes: (a) Lafrance, M.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 16496-16497.
15. (b) Lafrance, M.; Rowley, C. N.; Woo, T. K.; Fagnou, K. J. Am, Chem. Soc. 2006, 128, 8754-8755.
16. (c) Mukhopadhyay, S.; Rothenberg, G.; Gitis, D.; Baidossi, M.; Ponde, D. E.; Sasson, Y. J, Chem. Soc., Perkin Trans. 2 2000, 1809-1812.
17. (d) Campeau, L. C.; Rousseaux, S.; Fagnou, K. J. Am. Chem. Soc. 2005, 127, 18020-18021.
18. α-Arylation of carbonyls: (a) Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234-245.
19. (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382-12383.
20. (c) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108-11109.
21. 3C-H bonds via Pd(IV) intermediates: (a) Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154-13155.
22. (b) Shabashov, D.; Daugulis, O. Org. Lett. 2005, 7, 3657-3659.
23. (c) Reddy, B. V. S.; Reddy, L. R.; Corey, E. J. Org. Lett. 2006, 8, 3391-3394.
24. (d) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330-7331.
25. (e) Giri, R.; Maugel, N.; Li, J.-J.; Wang, D.-H.; Breazzano, S. P.; Saunders, L. B.; Yu, J.-Q. J. Am. Chem. Soc. 2007, 129, 3510-3511.
26. 3C-H bonds with alkylboron reagents: Chen, X.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 12634-12635.
27. 3C-H bond arylation: Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685-4696.
28. Direct arylations of α,β-unsaturated carbonyl compounds at the γ-position and of 4-alkylnitrobenzenes were reported. In the latter report, an example of direct arylation of 4-methylpyrimidine yielding 4-(diarylmethyl)pyrimidine was reported: (a) Terao, Y.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron Lett. 1998, 39, 6203-6206.
29. (b) Inoh, J.; Satoh, T.; Pivsa-Art, S.; Miura, M.; Nomura, M. Tetrahedron Lett. 1998, 39, 4673-4676.
30. Ruthenium-catalyzed arylation: Pastine, S. J.; Gribkov, D. V.; Sames, D. J. Am. Chem. Soc. 2006, 128, 14220-14221.
31. Copper-catalyzed oxidative functionalization: Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 6968-6969.
32. Pd-catalyzed arylation of cyclopentadienes: (a) Dyker, G.; Heiermann, J.; Miura, M.; Inoh, J.; Pivsa-Art, S.; Satoh, T.; Nomura, M. Chem.Eur. J. 2000, 6, 3426-3433.
33. (b) Dyker, G.; Heiermann, J.; Miura, M. Adv. Synth. Catal. 2003, 345, 1127-1132.
34. Pd-catalyzed intramolecular arylative cyclization: (a) Ren, H.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 3462-3465.
35. (b) Ren, H.; Li, Z.; Knochel, P. Chem. Asian J. 2007, 2, 416-433.
36. The effect of base is summarized in the Supporting Information.
37. The result of the ligand screening is tabulated in the Supporting Information.
38. Heitz, W.; Brugging, W.; Freund, L.; Gailberger, M.; Greiner, A.; Jung, H.; Kampschulte, U.; Niessner, N.; Osan, F.; Schmidt, H. W.; Wicker, M. Makromol. Chem. 1988, 189, 119-127.
39. The Friedel-Crafts arylation reaction of triarylmethanols or their analogues with aniline is the most popular method, (a) Zimmermann, T. J.; Müller, T. J. J. Synthesis 2002, 1157-1162.
40. (b) Su, D.; Menger, F. M. Tetrahedron Lett. 1997, 38, 1485-1488.
41. (c) Grimm, M.; Kirste, B.; Kurreck, H. Angew. Chem., Int. Ed. Engl. 1986, 25, 1097-1098.
42. 20 was used, we obtained moderate yields of 4f and 4g with contamination by byproducts. The byproducts were likely formed by ring opening of the oxazole and thiazole units.
43. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456-463.
44. Use of di(2-pyridyl)methane: Steel. P. J.; Sumby, C. J. Dalton 2003, 4505-4515 and refs cited therein.
45. Gornitzka, H.; Catherine, H.; Bertrand, G.; Pfeiffer, M.; Stalke, D. Organometallics 2000, 19, 112-114 and refs cited therein.
46. Triarylmethanes are typically prepared by (1) addition of aryl Grignard reagents to carbonyls yielding triarylmethanols and subsequent reduction of the hydroxy group under acidic conditions or (2) Friedel-Crafts arylaton of diarylmethanols. Muthyala, R.; Katritzky, A. R.; Lan, X. Dyes Pigm. 1994, 25, 303-324 and refs cited therein.