Palladium-catalyzed synthesis of symmetrical biaryls under microwave irradiation and conventional heating

Synthetic Communications

Volumn 43, Issue 9, 2013, Pages 1314-1327

  Hajipour, Abdol Reza ^a,b   Rafiee, Fatemeh ^a  

^a ISFAHAN UNIVERSITY OF TECHNOLOGY   (Iran)

^b UNIVERSITY OF WISCONSIN SCHOOL OF MEDICINE AND PUBLIC HEALTH   (United States)

Author keywords

Biaryls; cyclopalladated catalyst; homo coupling reaction; tribenzylamine

Indexed keywords

PALLADIUM;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; HEATING; MICROWAVE IRRADIATION;

EID: 84874501348     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2011.632830     Document Type: Article

References (30)

1. Bringmann, G.; Walter, R.; Weririch, R. The directed synthesis of biaryl compounds: Modern concepts and strategies. Angew. Chem., Int. Ed. Engl. 1990, 29, 971.
2. Lei, J. G.; Lin, G. Q. The first total synthesis of 4,4′- biisofraxidin. Chin. J. Chem. 2002, 20, 1263.
3. Suh, I. H.; Choi, S.; Lewis, D. E.; Jensen, W. P. Two related benzylcamphor dimmers. Acta Crystallogr. 1997, 53, 963.
4. Lehn, J. M. Supramolecular Chemistry, 1st ed.; VCH Verlasgesellschaft: Weinheim, Germany, 1995.
5. Chao, Y.; Weisman, G. R.; Sogah, G. D. Y.; Cram, D. J. Host-guest complexation, 21: Catalysis and chiral recognition through designed complexation of transition states in transacylations of amino ester salts. J. Am. Chem. Soc. 1979, 101, 4948.
6. 3 n+ hybrid material. Adv. Mater. 1996, 8, 497.
7. Lei, A.; Zhang, X. A novel palladium-catalyzed homocoupling reaction initiated by transmetallation of palladium enolates. Tetrahedron Lett. 2002, 43, 2525.
8. Seganish, W. M.; Mowery, M. E.; Riggleman, S.; DeShong, P. Palladium-catalyzed homocoupling of aryl halides in the presence of fluoride. Tetrahedron 2005, 61, 2117.
9. Tao, X. C.; Zhou, W.; Zhang, Y. P.; Dai, C. Y.; Shen, D.; Huang, M. Homocoupling of aryl bromides catalyzed by nickel chloride in pyridine. Chin. J. Chem. 2006, 24, 939.
10. Yanagisawa, A.; Hibino, H.; Habaue, S.; Hisada, Y.; Yamamoto, H. Highly selective homocoupling reaction of allylic halides using barium metal. J. Org. Chem. 1992, 57, 6386.
11. Ranu, B. C.; Dutta, P.; Sarkar, A. Indium-promoted reductive homocoupling of alkyl and aryl halides. Tetrahedron Lett. 1998, 39, 9557.
12. Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; John Wiley: New York, 1980.
13. 2-symmetric binaphthyls. J. Org. Chem. 1994, 59, 2655.
14. Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 1995, 95, 2457.
15. Negishi, E. Palladium-or nickel-catalyzed cross coupling: A new selective method for carbon-carbon bond formation. Acc. Chem. Res. 1982, 15, 340.
16. Farina, V. New perspectives in the cross-coupling reactions of organostannanes. Pure. Appl. Chem. 1996, 68, 73.
17. Percec, V.; Bae, J. Y.; Zhao, M.; Hill, D. H. Aryl mesylates in metal-catalyzed homocoupling and cross-coupling reactions, 1: Functional symmetrical biaryls from phenols via nickel-catalyzed homocoupling of their mesylates. J. Org. Chem. 1995, 60, 176.
18. Bedford, R. Palladacyclic catalysts in C-C and C-heteroatom bond-forming reactions. Chem. Commun. 2003, 9, 1787.
19. Qi, C.; Sun, X.; Lu, C.; Yang, J.; Du, Y.; Wu, H.; Zhang, X. M. Palladium-catalyzed reductive homocoupling reactions of aromatic halides in dimethyl sulfoxide (DMSO) solution. J. Organomet. Chem. 2009, 694, 2912.
20. 2) as Pd ligand and solvent for selective dehalogenation or homocoupling of aryl halides. J. Organomet. Chem. 2008, 693, 2469.
21. Navarro, O.; Marion, N.; Oonishi, Y.; Kelly III, R. A.; Nolan, S. P. Suzuki-Miyaura, α-ketone arylation and dehalogenation reactions catalyzed by a versatile N-heterocyclic carbene-palladacycle complex. J. Org. Chem. 2006, 71, 685.
22. Li, Q.; Nie, J.; Yang, F.; Zheng, R.; Zou, G.; Tang, J. Homocoupling of aryl iodides catalyzed by cyclopalladated complexes of tertiary arylamines. Chin. J. Chem. 2004, 22, 419.
23. Bedford, R. B.; Pilarski, L. T. Palladacyclic and platinacyclic catalysts for the allylation of aldehydes. Tetrahedron Lett. 2008, 49, 4216.
24. Kappe, C. O. Controlled microwave heating in modern organic synthesis. Angew. Chem. Int. Ed. 2004, 43, 6250.
25. Singh, B. K.; Kaval, N.; Tomar, S.; Eycken, E. V.; Parmar, V. S. Transition metal-catalyzed carbon-carbon bond-formation Suzuki, Heck, and Sonogashira reactions using microwave and microtechnology. Org. Process. Res. Dev. 2008, 12, 468.
26. Hajipour, A. R.; Karami, K.; Tavakoli, G. A comparative homocoupling reaction of aryl halides using monomeric orthopalladated complex of 4-methoxybenzoylmethylenetriphenylphosphorane under conventional and microwave irradiation conditions. Appl. Organomet. Chem. 2011, 25, 567
27. Fuchita, Y.; Yoshinaga, K.; Hanaki, T.; Kawano, H.; Kinoshita-Nagaoka, J. Cyclopalladation of mono-, di-, and tribenzylamine by palladium(II) acetate: Influence of bulkiness around the nitrogen atom of benzylamine upon internal metallation. J. Organomet. Chem. 1999, 580, 273.
28. Hajipour, A. R.; Rafiee, F. Application of dimeric cyclopalladated complex of tribenzylamine as an efficient catalyst in the Heck cross-coupling reaction. J. Organomet. Chem. 2011, 696, 2669.
29. Schareina, T.; Zapf, A.; Beller, M. Improving palladium-catalyzed cyanation of aryl halides: Development of a state-of-the-art methodology using potassium hexacyanoferrate(II) as cyanating agent. J. Organomet. Chem. 2004, 689, 4576.
30. Rosner, T.; Bars, J. L.; Pfaltz, A.; Blackmond, D. G. Kinetic studies of Heck coupling reactions using palladacycle catalysts: Experimental and kinetic modeling of the role of dimer species. J. Am. Chem. Soc. 2001, 123, 1848.