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Synthesis 2006(21): 3647-3653
DOI: 10.1055/s-2006-950209
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
Further Information
Received
2 June 2006
Publication Date:
21 August 2006 (online)
Publication History
Publication Date:
21 August 2006 (online)
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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.
Key words
aldehydes - arenes - condensation - furans - hydroarylation - indoles
- 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 SystemsDürr 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