Palladium-Catalyzed Cyanation Reactions of Thiophene Halides

Thomas Erker; Stephanie Nemec

doi:10.1055/s-2003-42490

SHORTPAPER

Palladium-Catalyzed Cyanation Reactions of Thiophene Halides

Thomas Erker*, Stephanie Nemec
Institute of Pharmaceutical Chemistry, University of Vienna, Althanstrasse 14, 1090 Vienna, Austria
Fax: +43(1)42779551; e-Mail: thomas.erker@univie.ac.at;

Abstract

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Abstract

The described method provides an efficient cyanation reaction of thiophene halides using tris(dibenzylidene-acetone)dipalladium(0), 1,1′-bis-(diphenylphosphino)ferrocene) and zinc powder as the catalyst system and Zn(CN)₂ as the cyanide source. Several thiophenes with various substituents are effectively cyanated under these conditions.

Key words

nitriles - thiophene - palladium - catalysis - cyanation

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References

1 Studies on the Chemistry of Thioannelated O,N- and S,N- containing heterocycles - Part 32. For Part 31, see: Erker T. Trinkl K. Scientia Pharmaceutica 2003, 71: 51

2a Mowry DT. Chem. Rev. 1948, 42: 189

2b Grashey R. Comp. Org. Chem. 1991, 6: 225

2c Okano T. Kiji J. Toyooka Y. Chem. Lett. 1998, 426

2d Anderson BA. Bell EC. Ginah FO. Harn NK. Pagh LM. Wepsiec JP. J. Org. Chem. 1998, 63: 8224

2e Tschaen DM. Desmond R. King AO. Fortin MC. Pipik B. King S. Verhoeven TR. Synth. Commun. 1994, 24: 887

3a Heck RF. Palladium Reagents in Organic Synthesis Academic; New York: 1985.

3b Chatani N. Hanafusa T. J. Org. Chem. 1986, 51: 4714

3c Sakamoto T. Oshawa K. J. Chem. Soc., Perkin Trans. 1 1999, 2323

4 Jin F. Confalone PN. Tetrahedron Lett. 2000, 41: 3271

5a Selnick AG. Smith GR. Tebben AJ. Synth. Commun. 1995, 25: 3255

5b Kubota H. Rice KC. Tetrahedron Lett. 1998, 39: 2970

6 Helbert M. Berthelot M. Laurence C. Spinelli D. Consiglio G. Amone C. Spectrochim. Acta, Part A 1983, 39: 703

7 Arakawa S. Veda N. Shigemasa Y. Nakashima R. Tottori Daigaku Nogakubu Kenkyu Hokoku 1982, 13: 69

8 Lohaus G. Chem. Ber. 1967, 100(8): 2719

9 Morel J. Paulmier C. Pastour P. C. R. Acad. Sci., Paris, Ser. C 1968, 266: 1300

10 Seth-Paul WA. Van der Veken BJ. Can. J. Spectrosc. 1978, 23: 74

11 Dubus P. Decroix B. Morel J. Paulmier C. C. R. Acad. Sci., Ser. C 1974, 278(1): 61

12 Baltrop JA. Day AC. Irving E. J. Chem. Soc., Chem. Commun. 1979, 20: 881

13 Fournari P. Guiland R. Person M. Bull. Soc. Chim. Fr. 1967, 11: 4115

14 Holland GF. inventors; U. S. Patent 4282246.

15 Suzuki H. Iwaro T. Sugiyama T. Bull. Inst. Chem. Res., Kyoto Univ. 1974, 52: 561