Rapid Synthesis of Aryl Azides from Aryl Halides under Mild Conditions

Jacob Andersen; Ulf Madsen; Fredrik Björkling; Xifu Liang

doi:10.1055/s-2005-872248

LETTER

Rapid Synthesis of Aryl Azides from Aryl Halides under Mild Conditions

Jacob Andersen^a, Ulf Madsen^b, Fredrik Björkling^a, Xifu Liang*^a
^a Department of Medicinal Chemistry, LEO Pharma, Industriparken 55, 2750 Ballerup, Denmark
Fax: +45(7226)3320; e-Mail: xifu.liang@leo-pharma.com;
^b Department of Medicinal Chemistry, The Danish University of Pharmaceutical Sciences, 2100 Copenhagen, Denmark

Abstract

All articles of this category

Abstract

A rapid synthesis of aryl azides from the corresponding aryl halides catalyzed by CuI/diamine is described. Sodium ascorbate was found to have a positive effect on stabilization of the catalyst system. The reactions were performed under very mild conditions generally with high yields. In the case of aryl iodides, the transformation could be carried out at room temperature.

Key words

copper - aryl azides - aryl halides - ligands - azidonation

Full Text

References

1 For a review, see: Scriven EV. Turnbull K. Chem. Rev. 1988, 88: 351

For recent examples, see:

2a Feldman AK. Colasson B. Fokin VV. Org. Lett. 2004, 6: 3897

2b Tornøe CW. Christensen C. Meldal M. J. Org. Chem. 2002, 67: 3057

2c Rostovtsev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 2596

2d Yadav JS. Subba Reddy BV. Geetha V. Synlett 2002, 513

For examples, see:

3a Alley SC. Ishmael FT. Jones AD. Benkovic SJ. J. Am. Chem. Soc. 2000, 122: 6126

3b Cho H. Park H. Zhang X. Riba I. Gaskell SJ. Widger WR. Kohn H. J. Org. Chem. 1997, 62: 5432

4 Rodrigues JAR. Abramovitch RA. de Souse JDF. Leiva GC. J. Org. Chem. 2004, 69: 2920

5a Smith PAS. Rowe CD. Bruner LB. J. Org. Chem. 1969, 34: 3430

5b Leroux F. Castagnetti E. Schlosser M. J. Org. Chem. 2003, 68: 4693

6a Fisher W. Anselme J.-P. J. Org. Chem. 1969, 34: 3430

6b Nielsen PE. Tetrahedron Lett. 1979, 20: 2705

7 Huber M.-L. Pinhey JT. J. Chem. Soc., Perkin Trans. 1 1990, 721

8 Liu Q. Tor T. Org. Lett. 2003, 5: 2571

9 Suzuki H. Miyoshi K. Shinoda M. Bull. Chem. Soc. Jpn. 1980, 53: 1765

10a Zhu W. Ma D. Chem. Commun. 2004, 888

10b Cai Q. Zhu W. Zhang H. Zhang Y. Ma D. Synthesis 2005, 498

For reviews, see:

11a Ley SV. Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400

11b Kunz K. Scholz U. Ganzer D. Synlett 2003, 2428

11c Lindley J. Tetrahedron 1984, 40: 1433

12a Antilla JC. Baskin JM. Barder TE. Buchwald SL. J. Org. Chem. 2004, 69: 5578

12b Jiang L. Job GE. Klapars A. Buchwald SL. Org. Lett. 2003, 5: 3667

12c Zanon J. Klapars A. Buchwald SL. J. Am. Chem. Soc. 2003, 125: 2890

12d Klapars A. Buchwald SL. J. Am. Chem. Soc. 2002, 124: 14844

12e Antilla JC. Klapars A. Buchwald SL. J. Am. Chem. Soc. 2002, 124: 11684

12f Klapars A. Huang X. Buchwald SL. J. Am. Chem. Soc. 2002, 124: 7421

13 A similar effect was found with the use of dba: Kiyomori A. Marcoux J.-F. Buchwald SL. Tetrahedron Lett. 1999, 40: 2657

14 Kurumi M. Sasaki K. Takata H. Nakayama T. Heterocycles 2000, 53: 2809

15 Zhmurova IN. Martynyuk AP. Kirsanov AV. J. Gen. Chem. USSR 1971, 41: 791

16 Spauchus H. Scott JM. J. Am. Chem. Soc. 1951, 73: 208