Triflic salt-catalyzed coupling: Iron triflate-catalyzed homocoupling of aryl bromides in the presence of metallic magnesium

Synthetic Communications

Volumn 40, Issue 17, 2010, Pages 2556-2563

  Zhang, Yan Yan ^a   Lin, Jing Du ^a   Xu, Xiao Liang ^a   Li, Jing Hua ^a  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Aromatic bromide; homocoupling; iron triflate

Indexed keywords

BROMIDE; IRON DERIVATIVE; MAGNESIUM DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYSIS; CATALYST; CROSS COUPLING REACTION; GRIGNARD REACTION; ONE POT SYNTHESIS; QUANTUM YIELD; REACTION ANALYSIS;

EID: 77955460982     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903289230     Document Type: Article

References (46)

1. Miyaura, N. Cross-Coupling Reactions. A Practical Guide Topics in Current Chemistry; Springer: Berlin 2002.
2. Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry: A Guide for the Synthetic Chemist; Elsevier: Oxford, 2000.
3. Suzuki, A. Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles. J. Organomet. Chem. 1999, 576(1-2), 147-168.
4. Duncton, M. A. J.; Pattenden, G. The intramolecular Stille reaction. J. Chem. Soc., Perkin Trans. 1 1999, 10, 1235-1246.
5. Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, Germany, 1998.
6. Knight, D. W. In Comprehensive Organic Synthesis; B. M. Trost, I. Fleming (Eds.); Pergamon: Oxford, 1991; vol.3, p. 481.
7. Stille, J. K. The palladium-catalyzed cross-coupling reactions of organotin reagents with organic electrophiles. Angew. Chem., Int. Ed. Engl. 1986, 25(6), 508-524.
8. Sainsbury, M. Modern methods of aryl-aryl bond formation. Tetrahedron 1980, 36(23), 3327-3359.
9. Fanta, P. E. The Ullmann synthesis of biaryls. Chem. Rev. 1946, 38(1), 139-196.
10. Fanta, P. E. The Ullmann synthesis of biaryls, 1945-1963: The asymmetric Ullmann reaction, 2: The synthesis of enantiomerically pure C2-symmetric binaphthyls. Chem. Rev. 1964, 64(6), 613-632.
11. Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; John Wiley: New York, 1980.
12. Nelson, T. D.; Meyers, A. I. The asymmetric Ullmann reaction, 2: The synthesis of enantiomerically pure C2-symmetric binaphthyls. J. Org. Chem. 1994, 59(9), 2655-2658.
13. Nicolaou, K. C.; Hanko, R.; Hartwig, W. (Eds). Handbook of Combinatorial Chemistry: Drugs, Catalysts, Materials; Wiley-VCH: Weinheim, Germany, 2002.
14. Negishi, E. (Ed.). Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley: New York 2002.
15. Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: New York, 1996.
16. Kochi, J. K. Homo coupling, disproportionation, and cross coupling of alkyl groups: Role of the transition metal catalyst. J. Organomet. Chem. 2002, 653(1-2), 11-19.
17. Smith, R. S.; Kochi, J. K. Mechanistic studies of iron catalysis in the cross coupling of alkenyl halides and Grignard reagents. J. Org. Chem. 1976, 41(3), 502-509.
18. Neumann, S. M.; Kochi, J. K. Synthesis of olefins: Cross-coupling of alkenyl halides and Grignard reagents catalyzed by iron complexes. J. Org. Chem. 1975, 40(5), 599-606.
19. Tamura, M.; Kochi, J. K. Vinylation of Grignard reagents: Catalysis by iron. J. Am. Chem. Soc. 1971, 93(6), 1487-1489.
20. Tamura, M.; Kochi, J. K. The reactions of Grignard reagents with transition metal halides: Coupling, disproportionation, and exchange with olefins. Bull. Chem. Soc. Jpn. 1971, 44(11), 3063-3073.
21. Tamura, M.; Kochi, J. K. Coupling of Grignard reagents with organic halides. Synthesis 1971, 6, 303-304.
22. Fuerstner, A.; Martin, R. Advances in iron-catalyzed cross-coupling reactions. Chem. Lett. 2005, 34(5), 624-629.
23. Shinokubo, H.; Oshima, K. E. Transition metal-catalyzed carbon-carbon bond formation with Grignard reagents: Novel reactions with a classic reagent. J. Org. Chem. 2004, 2004(10), 2081-2091.
24. Bolm, C.; Legros, J.; Le, P. J.; Zani, L. Iron-catalyzed reactions in organic synthesis. Chem. Rev. 2004, 104(12), 6217-6254.
25. Bica, K.; Gaertner, P. An iron-containing ionic liquid as recyclable catalyst for aryl Grignard cross-coupling of alkyl halides. Org. Lett. 2006, 8(4), 733-735.
26. Bedford, B. R.; Betham, M.; Bruce, W. D.; Danopoulos, A. A.; Frost, M. R.; Hird, M. Iron-phosphine,-phosphite,-arsine, and-carbene catalysts for the coupling of primary and secondary alkyl halides with aryl Grignard reagents. J. Org. Chem. 2006, 71(3), 1104-1110.
27. Bedford, B. R.; Bruce, W. D.; Frost, M. R. Simple iron-amine catalysts for the cross-coupling of aryl Grignards with alkyl halides bearing b-hydrogens. Chem. Commun. 2005, 33, 4161-4163.
28. Bedford, B. R.; Bruce, W. D.; Frost, M. R. Iron(III) salen-type catalysts for the cross-coupling of aryl Grignards with alkyl halides bearing b-hydrogens. Chem. Commun. 2004, 24, 2822-2823.
29. Martin, R.; Fürstner, A. Cross-coupling of alkyl halides with aryl Grignard reagents catalyzed by a low-valent iron complex. Angew. Chem., Int. Ed. 2004, 43(30), 3955-3957.
30. Nagano, T.; Hayashi, T. Iron-catalyzed Grignard cross-coupling with alkyl halides possessing b-hydrogens. Org. Lett. 2004, 6(8), 1297-1299.
31. Hojo, M.; Murakami, Y.; Aihara, H. Iron-catalyzed regio-and stereoselective carbolithia-tion of alkynes. Angew. Chem., Int. Ed. 2001, 40(3), 621-623. (Pubitemid 32144481)
32. Nakamura, M.; Hirai, A.; Nakamura, E. Iron-catalyzed olefin carbometalation. J. Am. Chem. Soc. 2000, 122(5), 978-979.
33. Cahiez, G.; Avedissian, H. Synthesis of functionalized triphenylenes by selective ether cleavage with b-bromocatecholborane. Synthesis 1998, 8, 1199-11122
34. Yanagisawa, A.; Nomura, N.; Yamamoto, H. Transition metal-catalyzed substitution reaction of allylic phosphates with Grignard reagents. Tetrahedron 1994, 50(20), 6017-6028.
35. N2 selective cross-coupling process. Synlett 1991, 7, 513-515.
36. Nagano, T.; Hayashi, T. Iron-catalyzed oxidative homo-coupling of aryl Grignard reagents. Org. Lett. 2005, 7(3), 491-493. (Pubitemid 40249298)
37. Cahiez, G.; Chaboche, C.; Mahuteau-Betzer, F.; Ahr, M. Iron-catalyzed homo-coupling of simple and functionalized arylmagnesium reagents. Org. Lett. 2005, 7(10), 1943-1946.
38. Xu, X.; Cheng, D.; Pei, W. Iron-catalyzed homocoupling of bromide compounds. J. Org. Chem. 2006, 71(17), 6637-6639.
39. Kobayashi, S.; Sugiura, M.; Kitagawa, H.; William, W. L. Rare-earth metal triflates in organic synthesis. Chem. Rev. 2002, 102(6), 2227-2302.
40. 3-catalyzed novel Mannich reaction of N-alkyoxycarbonylpyrrole or thiophene, formaldehyde, and primary amine hydrochlor-ide. Acta Chim. Sinica 2002, 60(3), 481-486.
41. Li, X.; Du, X.; Xu, Z. Toluene nitration catalyzed by metal triflates. Chin. J. Org. Chem. 2006, 26(8), 1111-1114.
42. Lin, J.; Zheng, Y.; Li, J. Preparation of (E)-6-(3-methyl-4- benzenesulfonyl-2-butenyl)-2,3,4,5-tetramethoxytoluene in the presence of trifluoromethanesulfonic salt. J. Zhejiang Univ. Technol. 2007, 35(2), 190-193.
43. Ma, N.; Zhu, Z.; Wu, Y. Cyclopalladated ferrocenylimine: A highly effective catalyst for the borylation Suzuki coupling reaction. Tetrahedron 2007, 63(22), 4625-4629.
44. Wang, L.; Zhang, Y.; Liu, L. Palladium-catalyzed homocoupling and cross-coupling reactions of aryl halides in poly(ethylene glycol). J. Org. Chem. 2006, 71(3), 1284-1287.
45. Tashiro, M.; Yamato, T. Studies on selective preparation of aromatic compounds, 20: Selective preparation of 2-mono-and 2,2-disubstituted biphenyl using the tert-butyl group as a positional protective group. J. Org. Chem. 1979, 44(17), 3037-3040.
46. Taylor, S. K.; Bennett, S. G.; Heinz, K. J. Coupling of aryl Grignard reagents by electron transfer to unsaturated 1,4-dihalo compounds. J. Org. Chem. 1981, 46(10), 2194-2196.