Efficient catalyst-free bi- and triaroylation of aromatic rings in a single step

Journal of Organic Chemistry

Volumn 73, Issue 22, 2008, Pages 9184-9187

  Lo Fiego, Marcos J ^a   Badajoz, Mercedes A ^a   Silbestri, Gustavo F ^a   Lockhart, María T ^a   Chopa, Alicia B ^a  

^a UNIVERSIDAD NACIONAL DEL SUR   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CHEMICAL REACTIONS; SYNTHESIS (CHEMICAL);

AROMATIC RINGS; CHEMICAL EQUATIONS; DICHLOROBENZENE; EFFICIENT CATALYSTS; ELECTROPHILIC AROMATIC SUBSTITUTIONS; EXCELLENT YIELDS; LEAVING GROUPS; REGIOSELECTIVE REACTIONS; SINGLE STEPS;

CATALYSIS;

1,4 PHENYLENEBIS(PHENYLMETHANONE); BENZENE DERIVATIVE; CARBON; KETONE DERIVATIVE; ORGANOTIN COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SOLVENT; TRIMETHYLTIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; DECOMPOSITION; REACTION TIME; SUBSTITUTION REACTION; SYNTHESIS;

CATALYSIS; HALOGENS; POLYCYCLIC HYDROCARBONS, AROMATIC; TIN COMPOUNDS;

EID: 56449097287     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801890e     Document Type: Article

References (18)

1. Smith, M. B.; March, J. March's Advanced Organic Chemistry; John Wiley: New York, 2001.
2. For a review, see: Dieter, K. Tetrahedron 1999, 55, 4177.
3. Rajakumar, P.; Srisailas, M.; Kanagalatha, R. Tetrahedron 2003, 59, 5365.
4. Rao, M. L. N.; Venkatesh, V.; Banerjee, D. Tetrahedron 2007, 63, 12917.
5. (a) Kawamoto, T.; Ejiri, S.; Kobayashi, K.; Odo, S.; Nishihara, Y.; Takagi, K. J. Org. Chem. 2008, 73, 1601.
6. (b) Saiga, A.; Hossain, K. M.; Takagi, K. Tetrahedron Lett. 2000, 41, 4629.
7. Pena, M. A.; Sestelo, J. P.; Sarandeses, L. A. Synthesis 2005, 485.
8. Silbestri, G. F.; Bogel Masson, R.; Lockhart, M. T.; Chopa, A. B. J. Organomet. Chem. 2006, 691, 1520.
9. Physical and spectroscopic data are in agreement with those previously reported: (a) Chopa, A. B.; Lockhart, M. T.; Silbestri, G. F. Organometallics 2001, 20, 3358.
10. (b) Chopa, A. B.; Lockhart, M. T.; Dorn, V. B. Organometallics 2002, 21, 1425.
11. (c) Fidelibus, P. M.; Silbestri, G. F.; Lockhart, M. T.; Mandolesi, S. D.; Chopa, A. B.; Podestá, J. P. Appl. Organometal. Chem. 2007, 21, 682.
12. Zhou, Q.-F.; Yang, F.; Guo, Q.-X.; Xue, S. Synlett 2007, 215.
13. (a) Zhao, W.; Carreira, E. M. Org. Lett. 2006, 8, 99.
14. (b) Higuchi, M.; Shomura, R.; Ohtsuka, Y.; Hayashi, A.; Yamamoto, K.; Kurth, D. Org. Lett. 2006, 8, 4723.
15. Yammal, C. C.; Podestá, J. C.; Rossi, R. A. J. Org. Chem. 1992, 57, 5720.
16. The coordinating ability of DMSO competes with the ketone improving the water solubility of trimethyltin chloride.
17. Organotin fluorides are relatively benign compounds.They are high melting, nonvolatile, insoluble (in both organic solvents and in water), and not easily absorbed through the skin; therefore, the risks of organotin fluorides are less than those of other organotins: Leibner, J. E.; Jacobus, J. J. Org. Chem. 1979, 44, 449.
18. Mitchell, T. N.; Kwetkat, K.; Godry, B. Organometallics 1991, 10, 1633.