Brönsted acid-catalyzed synthesis of diarylmethanes under non-genotoxic conditions

Tetrahedron Letters

Volumn 52, Issue 17, 2011, Pages 2235-2239

  Mendoza, Oscar ^a   Rossey, Guy ^a   Ghosez, Léon ^a  

^a NONE

Author keywords

Br nstedt acid catalysis; Diarylmethanes; Friedel Crafts benzylation; Triflic acid; Triflimide

Indexed keywords

BRONSTED ACID; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYST; SYNTHESIS;

EID: 79953213346     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.01.033     Document Type: Article

References (61)

1. Seminal paper: (a) Negishi, E.; King, A. O.; Okukado, N. J. Org. Chem. 1977, 42, 1821-1823;
2. Recent papers and references therein: (b) Paixao, M. W.; Braga, A. L.; Ludtke, D. S. J Br. Chem. Soc. 2008, 19, 813-830;
3. (c) Amatore, M.; Gosmini, C. Chem. Commun. 2008, 5019-5021;
4. (d) Bedford, R. B.; Huwe, M.; Wilkinson, M. C. Chem. Commun. 2009, 600-602;
5. (e) Salvi, L.; Kim, J. G.; Walsh, P. J. J. Am. Chem. Soc. 2009, 131, 12483-12493;
6. (f) Duplais, C.; Krasovskiy, A.; Wattenberg, A.; Lipshutz, B. H. Chem. Commun. 2010, 46, 562-564.
7. First reported example of a Suzuki-Miyaura coupling with a benzyl halide: (a) Maddaford, S. P.; Keay, B. A. J. Org. Chem. 1994, 59, 6501;
8. Recent examples and references cited therein: (b) Nobre, S. M.; Montiero, A. L. Tetrahedron Lett. 2004, 45, 8225;
9. (c) McLaughlin, M. Org. Lett. 2005, 4875-4878;
10. (d) Molander, G. A.; Elia, M. D. J. Org. Chem. 2006, 71, 9198-9202;
11. (e) Burns, J. M.; Fairlamb, I. J. S.; Kapdi, A. R.; Sehnal, P.; Taylor, J. R. K. Org. Lett. 2007, 9, 5397;
12. (f) Henry, N.; Enguehard-Gueiffer, C.; Thery, I.; Guieffier, A. Eur. J. Org. Chem. 2008, 4824-4827;
13. (g) Alacid, E.; Najera, C. J. Org. Chem. 2009, 74, 2321-2327.
14. (a) Friedel, C.; Crafts, J. M. C.R. Hebd. Séances Acad. Sci. 1877, 84, 1392;
15. (b) Friedel, C.; Crafts, J. M. C.R. Hebd. Séances Acad. Sci. 1877, 84, 1450;
16. (c) Olah, G. A. Friedel-Crafts and Related Reactions; Wiley: New York, 1963;
17. (d) Olah, G. A. Friedel-Crafts Chemistry; Wiley: New York, 1973;
18. (e) Roberts, R. M.; Khalaf, A. A. Friedel-Crafts Alkylation Chemistry; Marcel Dekker: New York, 1984;
19. (f) Olah, G. A.; Krishnamurti, R.; Surya Prakash, G. K., 1st ed. In Comprehensive Organic Synthesis; Pergamon: New York, 1991; Vol. 3,;
20. (g) Bandini, M; Melloni, A.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 550-556;
21. (h) Bandini, M.; Emer, E.; Tommasi, S.; Umani-Ronchi, A. Eur. J. Org. Chem. 2006, 3527-3544;
22. (i) Kaneko, M.; Hayashi, R.; Cook, G. R. Tetrahedron Lett. 2007, 48, 7085-7087.
23. (a) Tsuchimoto, T.; Tobita, K.; Hiyama, T.; Fukuzawa, S.-I. Synlett 1996, 557-559;
24. (b) Nakano, M.; Matsuo, J.-i.; Mukaiyama, T. Chem. Lett. 2000, 29, 1352-1353;
25. (c) De la Cruz, M. H. C.; Da Silva, J. F. C.; Lachter, E. R. Appl. Catal. A: Gen. 2003, 245, 377-382;
26. (d) Smith, K.; El-Hiti, G. A. Curr. Org. Synth. 2004, 1, 253-274;
27. (e) Yi, W.-B.; Cai, C. J. Fluorine Chem. 2005, 126, 831-833;
28. (f) Mantri, K.; Komura, K.; Kubota1, Y.; Sugi, Y. J. Mol. Catal. A: Chem. 2005, 236, 168-175;
29. (g) Mertins, K.; Iovel, I.; Kischel, J.; Zapf, A.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 238-242;
30. (h) Iovel, I.; Kischel, J.; Zapf, A.; Beller, M. Adv. Synth. Catal. 2006, 348, 691-695;
31. (i) Rueping, M.; Nachtsheim, B. J.; Ieawsuwan, W. Adv. Synth. Catal. 2006, 348, 1033-1037;
32. (j) Sun, H. B.; Li, B.; Chen, S. J.; Li, J.; Hua, R. M. Tetrahedron 2007, 63, 10185-10188;
33. (k) Podder, S.; Choudhury, J.; Roy, S. J. Org. Chem. 2007, 72, 3129-3132;
34. (l) Zhang, C.; Gao, X.; Zhang, J.; Peng, X. Synlett 2010, 261-265.
35. (a) Gihani, M. T. E.; Heaney, H.; Shuhaibar, K. F. Synlett 1996, 871-872;
36. (b) Fukuzawa, S. I.; Tsuchimoto, T.; Hiyama, T. J. Org. Chem. 1997, 62, 151-156;
37. (c) Tsuchimoto, T.; Tobita, K.; Hiyama, T.; Fukuzawa, S. I. J. Org. Chem. 1997, 62, 6997-7005;
38. (d) Sharma, G. V. M.; Mahalingam, A. K. J. Org. Chem. 1999, 64, 8943-8944;
39. (e) Shiina, I.; Suzuki, M. Tetrahedron Lett. 2002, 43, 6391-6394;
40. (f) Noji, M.; Ohno, T.; Fuji, K.; Futabe, N.; Tajima, H.; Ishii, K. J. Org. Chem. 2003, 68, 9340-9347;
41. (g) Mukaiyama, T.; Kamiyama, H.; Yamanaka, H. Chem. Lett. 2003, 32, 814-815.
42. Iovel, I.; Mertins, K.; Kischel, J.; Zapf, A.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 3913-3917.
43. Sun, G.; Wang, Z. Tetrahedron Lett. 2008, 49, 4929-4932.
44. (a) Kamalakar, G.; Komura, K.; Kubota, Y.; Sugi, Y. J. Chem. Technol. Biotechnol. 2006, 81, 981-988;
45. (b) Mantri, K.; Komura, K.; Kubota, Y.; Sugi, Y. J. Mol. Catal. A: Chem. 2005, 236, 168-175;
46. (c) Olah, G. A.; Yamato J. Org. Chem. 1991, 56, 2089-2091.
47. Mathieu, B.; Ghosez, L. Tetrahedron Lett. 1997, 38, 5497-5500.
48. Ishii, A.; Kotera, O.; Saeki, T.; Mikami, K. Synlett 1997, 1145-1146.
49. For examples of Brönstedt acid catalysis of arylation of benzyl alcohol, see: (a) Shirakawa, S.; Kobayashi, S. Org. Lett. 2007, 9, 311-314;
50. (b) McCubbin, J. A.; Krokhin, O. V. Tetrahedron Lett. 2010, 51, 2447-2449.
51. Mendoza, O.; Rossey, G.; Ghosez, L. Tetrahedron Lett. 2010, 51, 9561-9564. and references cited therein.
52. Fu, T.-H.; Bonaparte, A.; Martin, S. F. Tetrahedron Lett. 2009, 50, 3253-3257.
53. (a) Marques da Silva, M. S.; Lucas da Costa, C.; de Magdala Pinto, M.; Lachter, E. R. React. Polymers 1995, 25, 55-61;
54. (b) Morais, M.; Torres, E. F.; Carmo, L. M. P. M.; Pastura, N. M. R.; Gonzales, W. A.; dos Santos, A. C. B.; Lachter, E. R. Catal. Today 1996, 28, 17-21.
55. Sarca, V. D.; Laali, K. K. Green Chem. 2006, 8, 615-620.
56. For other examples showing that HNTf2 often gives cleaner chemistry than HOTf, see: (a) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 1045;
57. (b) Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2004, 128, 10204-10205;
58. (c) Li, W.; Shi, M.; Li, Y. Chem. Eur. J. 2009, 15, 8852;
59. (d) Lemechko, P.; Grau, F.; Antoniotti, S.; Dunach, E. Tetrahedron Lett. 2007, 48, 5731.
60. 1H NMR and GC-MS. Purification by column chromatography gave 484 mg (85% yield) of bis(4-methoxyphenyl)methane, which was identical to an authentic sample.
61. +), found: 310.9655.