Synthesis 2006(21): 3647-3653  
DOI: 10.1055/s-2006-950209
PAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient Condensation Reactions of Electron-Rich Arenes with Aldehydes and Enals Promoted by Gold(III) Chloride: Practical Synthesis of Triaryl- and Triheteroarylmethanes and Related Compounds

Vijay Nair*, N. Vidya, K. G. Abhilasha
Organic Chemistry Division, Regional Research Laboratory (CSIR), Trivandrum 695019, India
Fax: 91(471)2491712; e-Mail: vijaynair_2001@yahoo.com;
Further Information

Publication History

Received 2 June 2006
Publication Date:
21 August 2006 (eFirst)

Abstract

Electron-rich arenes undergo gold(III) catalyzed condensation reactions with aldehydes and enals to afford bis- and tris-addition products, respectively, in high yields.

    References

  • 1 Kharasch MS. Isbell HS. J. Am. Chem. Soc.  1931,  53:  3053 
  • 2 Hashmi ASK. Schwarz L. Choi J.-H. Frost TM. Angew. Chem. Int. Ed.  2000,  39:  2285 
  • 3a Reetz TM. Sommer K. Eur. J. Org. Chem.  2003,  3485 
  • 3b Shi Z. He C. J. Org. Chem.  2004,  69:  3669 
  • 4a Luo Y. Li C.-J. Chem. Commun.  2004,  1930 
  • 4b Yao X. Li C.-J. J. Am. Chem. Soc.  2004,  126:  6884 
  • For reviews, see:
  • 5a Dyker G. Angew. Chem. Int. Ed.  2000,  39:  4237 
  • 5b Hashmi ASK. Gold Bull.  2003,  36:  3 
  • 5c Hashmi ASK. Gold Bull.  2004,  37:  51 
  • 5d Arcadi A. Guiseppe SD. Curr. Org. Chem.  2004,  8:  795 
  • 5e Hoffmann-Röder A. Krause N. Org. Biomol. Chem.  2005,  3:  387 
  • 5f Hashmi ASK. Angew. Chem. Int. Ed.  2005,  44:  6990 
  • 6a Nair V. Thomas S. Mathew SC. Org. Lett.  2004,  6:  3513 
  • 6b Nair V. Thomas S. Mathew SC. Vidya N. Rath NP. Tetrahedron  2005,  61:  9533 
  • 7 Gomberg M. J. Am. Chem. Soc.  1900,  22:  757 
  • 8 Nair V. Thomas S. Mathew SC. Abhilash KG. Tetrahedron  2006,  62:  6731 
  • 9a Rys P. Zollinger H. Fundamentals of the Chemistry and Application of Dyes   Wiley-Interscience; New York: 1972. 
  • 9b Muthyala R. Lan X. Dyes Pigm.  1994,  25:  303 
  • 10 Katritzky AR. Xie L. Fan W.-Q. J. Org. Chem.  1993,  58:  4376 
  • 11 Greene TW. Wuts PGM. Protective Groups in Organic Synthesis   3rd Ed.:  Wiley; New York: 1999. 
  • 12a Aldag R. Photochromism based on dissociation processes, In Photochromism: Molecules and Systems   Dürr H. Bouas-Laurent H. Elsevier; London: 1990. 
  • 12b Irie M. J. Am. Chem. Soc.  1983,  105:  2078 
  • 13 Mibu N. Sumoto K. Chem. Pharm. Bull.  2000,  48:  1810 
  • 14a Schick JW. Crowley DJ. J. Am. Chem. Soc.  1951,  73:  1377 
  • 14b Ungnade HE. Crandall EW. J. Am. Chem. Soc.  1949,  71:  2209 
  • 14c Pratt EF. Green LQ. J. Am. Chem. Soc.  1953,  75:  275 
  • 15a Katritzky AR. Gupta V. Garot C. Stevens CV. Gordeev MF. Heterocycles  1994,  38:  345 
  • 15b Katritzky AR. Toader D. J. Org. Chem.  1997,  62:  4137 
  • 16 Nair V. Abhilash KG. Vidya N. Org. Lett.  2005,  7:  5857 
  • 17 For another report, see: Hashmi ASK. Schwarz L. Rubenbauer P. Blanco MC. Adv. Synth. Catal.  2006,  348:  705 
  • 18 For the synthesis of aryl-gold(III) complexes from aromatic hydrocarbons, see: Nair V. Vidya N. Abhilash KG. Tetrahedron Lett.  2006,  47:  2871 
  • 19 Fuchita Y. Utsunomiya Y. Yasutake M. J. Chem. Soc., Dalton Trans.  2001,  2330 ; see also ref. 2
  • 20 Lo KK.-W. Tsang KH.-K. Hui W.-K. Zhu N. Chem. Commun.  2003,  2704 
  • 21 Plimmer JR. Gammon DW. Ragsdale NN. Encyclopedia of Agrochemicals   Vol. 3:  John Wiley and Sons; New York: 2003. 
  • 22 Ramirez A. Garcia-Rubio S. Curr. Med. Chem.  2003,  10:  1891 
  • 23a Moore RE. Cheuk C. Patterson GML. J. Am. Chem. Soc.  1984,  106:  6456 
  • 23b Fukuyama T. Chen X. J. Am. Chem. Soc.  1994,  116:  3125