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.

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