Cross-Coupling Reaction of Iodo-1,2,3-triazoles Catalyzed by Palladium

Juan Deng; Yong-Ming Wu; Qing-Yun Chen

doi:10.1055/s-2005-872119

PAPER

Cross-Coupling Reaction of Iodo-1,2,3-triazoles Catalyzed by Palladium

Juan Deng, Yong-Ming Wu*, Qing-Yun Chen*
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Rd, Shanghai 200032, P. R. China
Fax: +86(21)64166128; e-Mail: ymwu@mail.sioc.ac.cn ;

Abstract

All articles of this category

Abstract

The Suzuki, Heck and Sonogashira reactions of 1,4-disubstituted 5-iodo-1,2,3-trizaoles were studied. A versatile method for regioselective synthesis of 1,4,5-trisubstituted-1,2,3-triazoles was developed.

Key Words

Suzuki reaction - Heck reaction - Sonogashira reaction - palladium - 1,2,3-trizaoles

Full Text

References

1a Metal-Catalyzed Cross-Coupling Reactions Diederich F. Stang PJ. Wiley-VCH; Weinheim: 1998.

1b Tsuji J. Transition Metal Reagents and Catalysts: Innovation in Organic Synthesis Wiley; Chichester: 1995.

1c Miyaura N. Top. Curr. Chem. 2002, 219: 1

2a Handbook of Organopalladium Chemistry for Organic Synthesis Negishi E. Wiley-Interscience; New York: 2002.

2b Tsuji J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century Wiley; Chichester: 2004.

3a Madin A. O’Donnell CJ. Oh T. Old DW. Overman LE. Sharp MJ. Angew. Chem. Int. Ed. 1999, 38: 2934

3b Hynes J. Overman LE. Nasser T. Rucker PV. Tetrahedron Lett. 1998, 39: 4647

3c Hong CY. Overman LE. Romero A. Tetrahedron Lett. 1997, 38: 8439

4a Wu GG. Wong YS. Poirier M. Org. Lett. 1999, 1: 745

4b Smith GB. Dezeny GC. Hughes DL. King AO. Verhoeven TR. J. Org. Chem. 1994, 59: 8151

5a Kadnikov DV. Larock RC. Org. Lett. 2000, 2: 3643

5b Lopez-Dober MP. Castedo L. Granja JR. Org. Lett. 2001, 3: 2823

5c Novak Z. Szabo A. Rapasi J. Kotschy A. J. Org. Chem. 2003, 68: 3327

6 Dakin LA. Langille NF. Panek JS. J. Org. Chem. 2002, 67: 6812

7 Branu RU. Zeilter K. Muller TJJ. Org. Lett. 2001, 3: 3297

8 Sarkar A. Okada S. Nakanishi H. Matsuda H. Helv. Chim. Acta 1999, 82: 138

9 Yue D. Larock RC. J. Org. Chem. 2002, 67: 1905

10a Ohta A. Akita Y. Ohkuwa T. Chiba M. Fukunaga R. Miyafuji A. Nakata T. Tani N. Aoyagi Y. Heterocycles 1990, 31: 1951

10b Aoyagi Y. Inoue A. Koizumi I. Hashimoto R. Tokunaga K. Gohma K. Komatsu J. Sekine K. Miyafuji A. Kunoh J. Honma R. Akita Y. Ohta A. Heterocycles 1992, 33: 257

11 Gelman D. Tsvelikhovsky D. Molander GA. Blum J. J. Org. Chem. 2002, 67: 6287

12 Tan JQ. Chang JH. Demg MZ. Chinese J. Chem. 2004, 22: 941 ; Chem. Abstr. 2004, 140: 145997

13 Fan W.-Q. Katritzky AR. In Comprehensive Heterocyclic Chemistry II Vol. 4: Katritzky AR. Rees CW. Scriven WV. Elsevier; Oxford: 1996. p.1-126

14 Alvarez R. Velazquez S. San F. Aquaro S. De C. Perno CF. Karlesson A. Balzarini J. Camarasa MJ. J. Med. Chem. 1994, 37: 4185

15 Genin MJ. Allwine DA. Anderson DJ. Barbachyn MR. Emmert DE. Garmon SA. Graber DR. Grega KC. Hester JB. Hutchinson DK. Morris J. Reischer RJ. Ford CW. Zurenco GE. Hamel JC. Schaadt RD. Stapertand D. Yagi BH. J. Med. Chem. 2000, 43: 953

16 Brockunier LL. Parmee ER. Ok HO. Candelore MR. Cascieri MA. Colwell LF. Deng L. Feeney WP. Forest MJ. Hom GJ. MacIntyre DE. Tota LM. Wyvratt J. Fisher MH. Weber AE. Bioorg. Med. Chem. Lett. 2000, 10: 2111

17a Katritzky AR. Zhang Y. Singh SK. Heterocycles 2003, 60: 1225

17b Gothelf KV. Jørgensen KA. Chem. Rev. 1998, 98: 863

18a Rostovtsev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 2596

18b Tornøe CW. Christensen C. Meldal M. J. Org. Chem. 2002, 67: 3057

18c Wang Q. Chan TR. Hilgraf R. Fokin VV. Sharpless KB. Finn MG. J. Am. Chem. Soc. 2003, 125: 3192

18d Lober S. Rodriguez-Loaiza P. Gmeiner P. Org. Lett. 2003, 5: 1753

18e Pérez-Balderas F. Ortega-Munoz M. Morales-Sanfrutos J. Hernández-Mateo F. Calvo-Flores FG. Calvo-Asín JA. Isac-García J. Santoyo-González F. Org. Lett. 2003, 5: 1951

18f Krasinski A. Fokin VV. Sharpless KB. Org. Lett. 2004, 6: 1237

18g Kamijo S. Jin T. Huo Z. Yamamoto Y. J. Am. Chem. Soc. 2003, 125: 7786

18h Kamijo S. Jin T. Huo Z. Yamamoto Y. J. Org. Chem. 2004, 69: 2386

18i Appukkuttan P. Dehaen F. Wim VV. Van der Eycken E. Org. Lett. 2004, 6: 4223

19a Wu YM. Deng J. Fang X. Chen QY. J. Fluorine Chem. 2004, 125: 1415

19b Wu YM. Deng J. Li Y. Chen QY. Synthesis 2005, in press

For reviews see:

20a Suzuki A. J. Organomet. Chem. 1999, 576: 147

20b Miyaura N. In Advances in Metal-Organic Chemistry Vol. 6: Liebeskind LS. JAI Press; London: 1998. p.187-243

20c Suzuki A. In Metal-Catalyzed Cross-Coupling Reactions Diederich A. Stang PJ. Wiley-VCH; New York: 1998. Chap. 2.

20d Standforth SP. Tetrahedron 1998, 54: 163

20e Miyaura N. Suzuki A. Chem. Rev. 1995, 95: 2457

For reviews, see:

21a de Meijere A. Meyer FE. Angew. Chem., Int. Ed. Engl. 1994, 33: 2379

21b de Meijere A. Bräse S. J. Organomet. Chem. 1999, 576: 88

21c Cacchi S. J. Organomet. Chem. 1999, 576: 111

21d Negishi E.-i. Copéret C. Ma SM. Liou SY. Liu F. Chem. Rev. 1996, 96: 365

21e Heck RF. Org. React. 1982, 27: 345

21f Beletskaya IP. Cheprakov AV. Chem. Rev. 2000, 100: 3009

21g Whitcombe NJ. Hii KK. Gibson SE. Tetrahedron 2001, 57: 7449

The silver salt effect for enhancing the reaction rate for Heck type reactions has been first reported for the arylation of vinyl and allyl trimethylsilanes:

22a Karabelas K. Hallberg A. Tetrahedron Lett. 1985, 26: 3131

22b Karabelas K. Westerlund C. Hallberg A. J. Org. Chem. 1985, 50: 3896

22c Karabelas K. Hallberg A. J. Org. Chem. 1986, 51: 5286

23a Jeffery T. J. Chem. Soc., Chem. Commun. 1984, 1287

23b Jeffery T. Tetrahedron Lett. 1985, 26: 2667

23c Jeffery T. Tetrahedron Lett. 1991, 32: 2121

For reviews, see:

24a Sonogashira K. In Metal-Catalyzed Cross-Coupling Reactions Diederich F. Stang PJ. Wiley-VCH; New York: 1998. Chap. 5.

24b Brandsma L. Vasilevsky SF. Verkruijsse HD. In Application of Transition Metal Catalysts in Organic Synthesis Springer; New York: 1998. Chap. 10.

24c Rossi R. Carpita A. Bellina F. Org. Prep. Proced. Int. 1995, 27: 127

24d Sonogashira K. In Comprehensive Organic Synthesis Vol. 3: Trost BM. Fleming I. Pergamon; New York: 1991. Chap. 2.4.

24e Negishi E. Anastasia L. Chem. Rev. 2003, 103: 1979