A Convenient and General Synthesis of Cata- and Peri-Condensed Polycyclic Aromatic Hydrocarbons with a Fjord-Region

Abstract

Cata- and peri-condensed polycyclic aromatic hydrocarbons (PAHs) 10a-d and 11 have been conveniently synthesized by the application of Suzuki cross-coupling reaction. In three to four steps, these PAHs having fjord-region were obtained in an overall yield of 35-51% from commercially or easily accessible aryl boronic acids and aryl bromides.

Key words

polycyclic aromatic hydrocarbons - aryl boronic acids - Suzuki cross-coupling reaction - 2-(aryl)benzaldehyde - dibenzo[c,mno]chrysene - naphtho[8,1,2-ghi]chrysene

References

• 1 Harvey RG. Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity: Cambridge University Press   Cambridge; England: 1991.  Chap. 3.
• 2 Chang HF. Cho BP. J. Org. Chem.  1999,  64:  9051 
• 3 Agarwal SK. Sayer JM. Yeh HJC. Pannell LK. Hilton BD. Pigott MA. Dipple A. Yagi H. Jerina DM. J. Am. Chem. Soc.  1987,  109:  2497 
• 4 Harvey RG. Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity   Cambridge University Press; Cambridge: 1991.  Chaps. 7-10.
• 5 Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 
• 6 Kumar S. J. Org. Chem.  1997,  62:  8535 
• 7 Borredon E. Delmas M. Gaset A. Tetrahedron Lett.  1982,  23:  5283 
• 8 Pan H.-L. Fletcher TL. Synthesis  1973,  610 
• 9 Konieczny M. Harvey RG. J. Org. Chem.  1979,  44:  2158 
• 10 Cook JW. J. Chem. Soc.  1931,  2524 
• 11 Hayward RJ. Hopkinson AC. Leznoff CC. Tetrahedron  1972,  28:  439 

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Seidel A.; Biochemical Institute for Environmental Carcinogens, Lurup 4, 22927, Grosshansdorf, Germany.