Palladium-Catalyzed Synthesis of Water-Soluble Symmetric 9,10-Disubstituted Anthracenes

Abstract

The palladium-catalyzed coupling of 9,10-dibromoanthracene with α,β-unsaturated esters, sulfonates, and sulfonamides forms symmetric 9,10-dialkyl substituted anthracenes in good yield. Conversion of these compounds to the corresponding carboxylic and sulfonic acids gives water-soluble symmetric 9,10-disubstituted anthracenes.

Key words

organometallic chemistry - palladium - Heck reaction - anthracenes - dienes

References

• 1 Tsuji J. Palladium Reagents and Catalysts: Innovation in Organic Synthesis   1st ed.:  Wiley; New York: 1995. 
• 2a Kotha S. Ghosh AK. Synlett  2002,  451 
• 2b Kauffman JM. Synthesis  2001,  197 
• 2c Wagner G. Herrmann R. Scherer W. J. Organomet. Chem.  1996,  516:  225 
• 2d Tanaka K. Endo K. Aoyama Y. Chem. Lett.  1999,  887 
• 3 Xu Y. Alavanja MM. Johnson VL. Yasaki G. King SB. Tetrahedron Lett.  2000,  41:  4265 
• 4 Botsivali M. Evans DF. J. Chem. Soc., Chem. Commun.  1979,  1114 
• 5a Fukuda Y. Seto S. Furuta H. Ebisu H. Oomori Y. Terashima S. J. Med. Chem.  2001,  44:  1396 
• 5b Wunz TP. Dorr RT. Alberts DS. Tunget CL. Einspahr J. Milton S. Remers WA. J. Med. Chem.  1987,  30:  1313 
• 5c Murdock KC. Child RG. Lin Y. Warren JD. Fabio PF. Lee VJ. Izzo PT. Lang SA. Angier RB. Citarella RV. Wallace RE. Durr FE. J. Med. Chem.  1982,  25:  505 
• 6 Weitzel W. Mullen K. Makromol. Chem.  1990,  191:  2837 
• 7 Arcadi A. Bernocchi E. Cacchi S. Synlett  1991,  27 
• 8a Sharifi MM. Iran. J. Chem. & Chem. Eng.  1990,  13:  4 ; Chem. Abstr. 1991, 115, 207627
• 8b Miller MW. Amidon RW. J. Am. Chem. Soc.  1955,  77:  2845 
• 9a Marchand-Brynaert J. Bouchet M. Touillaux R. Beauve C. Fastrez J. Tetrahedron  1996,  37:  5591 
• 9b Whitmore WF. Landau EF. J. Am. Chem. Soc.  1946,  68:  1797