3-Acetylcoumarin as a Practical
Ligand for Copper-Catalyzed C-N Coupling Reactions at Room
Temperature

Chuan-Zhou Tao; Wei-Wei Liu; Ji-You Sun; Zhi-Ling Cao; Hui Li; Ying-Fen Zhang

doi:10.1055/s-0029-1218661

PAPER

3-Acetylcoumarin as a Practical Ligand for Copper-Catalyzed C-N Coupling Reactions at Room Temperature

Chuan-Zhou Tao*^a,b, Wei-Wei Liu^a, Ji-You Sun^a, Zhi-Ling Cao^a, Hui Li^a, Ying-Fen Zhang^a
^a Department of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, P. R. of China
^b Jiangsu Key Laboratory of Marine Biotechnology, Huaihai Institute of Technology, Lianyungang 222005, P. R. of China
Fax: +86(518)85895403; e-Mail: cztao@mail.ustc.edu.cn;

Abstract

All articles of this category

Abstract

The use of coumarin-based ligands was examined in copper-catalyzed C-N cross-coupling reactions. It was found that 3-acetylcoumarin constituted a new, practical ligand for the copper-catalyzed N-arylation of aliphatic amines and imidazole with aryl iodides at room temperature. Aryl bromides could also be aminated efficiently at 80 ˚C. This readily available catalyst system, namely copper(I) iodide and 3-acetylcoumarin, provides a mild and practical method for the synthesis of aromatic amines.

Key words

copper - catalysis - cross-coupling - 3-acetylcoumarin - room temperature

Full Text

References

1 Negwer M. Organic-chemical Drugs and their Synonyms: (An International Survey) 7th ed.: Akademie; Berlin: 1994.

2a Wolfe JP. Wagaw S. Marcoux JF. Buchwald SL. Acc. Chem. Res. 1998, 31: 805

2b Hartwig JF. Angew. Chem. Int. Ed. 1998, 37: 2046

2c Schlummer B. Scholz U. Adv. Synth. Catal. 2004, 346: 1599

2d Tewari A. Hein M. Zapf A. Beller M. Tetrahedron 2005, 61: 9705

2e Charles MD. Schultz P. Buchwald SL. Org. Lett. 2005, 7: 3965

2f Nicolaou KC. Bulger PG. Sarlah D. Angew. Chem. Int. Ed. 2005, 44: 4442

2g Shen Q. Shekhar S. Stambuli JP. Hartwig JF. Angew. Chem. Int. Ed. 2005, 44: 1371

2h Fang YQ. Lautens M. Org. Lett. 2005, 7: 3549

2i Altman RA. Koval ED. Buchwald SL. J. Org. Chem. 2007, 72: 6190

2j Altman RA. Hyde AM. Huang X. Buchwald SL. J. Am. Chem. Soc. 2008, 130: 9613

2k Shen Q. Ogata T. Hartwig JF. J. Am. Chem. Soc. 2008, 130: 6586

2l Bertrand MB. Neukom JD. Wolfe JP. J. Org. Chem. 2008, 73: 8851

3a Lindley J. Tetrahedron 1984, 40: 1433

3b Hassan J. Sevignon M. Gozzi C. Schulz E. Lemaire M. Chem. Rev. 2002, 102: 1359

3c Ley SV. Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400

3d Deng W. Wang YF. Zou Y. Liu L. Guo QX. Tetrahedron Lett. 2004, 45: 2311

3e Yang T. Lin C. Fu H. Org. Lett. 2005, 7: 4781

3f Deng W. Liu L. Zhang C. Liu M. Guo QX. Tetrahedron Lett. 2005, 46: 7295

3g Lv X. Wang Z. Bao W. Tetrahedron 2006, 62: 4756

3h Altman RA. Buchwald SL. Org. Lett. 2006, 8: 2779

3i Correa A. Bolm C. Adv. Synth. Catal. 2007, 349: 2673

3j Ma HC. Jiang XZ. J. Org. Chem. 2007, 72: 8943

3k Zhang SL. Liu L. Fu Y. Guo QX. Organometallics 2007, 26: 4546

3l Mao J. Guo J. Song H. Ji SJ. Tetrahedron 2008, 64: 1383

3m Huang YZ. Gao J. Ma H. Miao H. Xu J. Tetrahedron Lett. 2008, 49: 948

3n Yang C.-T. Fu Y. Huang Y.-B. Yi J. Guo Q.-X. Liu L. Angew. Chem. Int. Ed. 2009, 48: 7398

4a Kunz K. Scholz U. Ganzer D. Synlett 2003, 2428

4b Deng W. Liu L. Guo QX. Chin. J. Org. Chem. 2004, 24: 150

4c Beletskaya IP. Cheprakov AV. Coord. Chem. Rev. 2004, 248: 2337

4d Evano G. Blanchard N. Toumi M. Chem. Rev. 2008, 108: 3054

4e Monnier F. Taillefer M. Angew. Chem. Int. Ed. 2009, 48: 6954

5 Kwong FY. Buchwald SL. Org. Lett. 2003, 5: 793

6a Ma D. Zhang Y. Yao J. Wu S. Tao F. J. Am. Chem. Soc. 1998, 120: 12459

6b Ma D. Cai Q. Zhang H. Org. Lett. 2003, 5: 2453

6c Zhang H. Cai Q. Ma D. J. Org. Chem. 2005, 70: 5164

7a Lu Z. Twieg RJ. Huang SD. Tetrahedron Lett. 2003, 44: 6289

7b Lu Z. Twieg RJ. Tetrahedron 2005, 61: 903

8 Zhang Z. Mao J. Zhu D. Wu F. Chen H. Wan B. Tetrahedron 2006, 62: 4435

9 Xu L. Zhu D. Wu F. Wang R. Wan B. Tetrahedron 2005, 61: 6553

10 Shafir A. Buchwald SL. J. Am. Chem. Soc. 2006, 128: 8742

11 Jiang D. Fu H. Jiang Y. Zhao Y. J. Org. Chem. 2007, 72: 672

12 Wang D. Ding K. Chem. Commun. 2009, 1891

13a Wu JS. Liu WM. Zhuang XQ. Wang F. Wang PF. Tao SL. Zhang XH. Wu SK. Lee ST. Org. Lett. 2007, 9: 33

13b Roussakis E. Pergantis SA. Katerinopoulos HE. Chem. Commun. 2008, 6221

13c Ray D. Bharadwaj PK. Inorg. Chem. 2008, 47: 2252

13d Berkel SSV. Lee BVD. Delft FLV. Rutjes FPJT. Chem. Commun. 2009, 4272

13e Mizukami S. Okada S. Kimura S. Kikuchi K. Inorg. Chem. 2009, 48: 7630

13f Jung HS. Kwon PS. Lee JW. Kim JI. Hong CS. Kim JW. Yan S. Lee JY. Lee JH. Joo T. Kim JS. J. Am. Chem. Soc. 2009, 131: 2008

14 Hollmann D. Bahn S. Tillack A. Beller M. Angew. Chem. Int. Ed. 2007, 46: 8291

15 Okano K. Tokuyama H. Fukuyama T. Org. Lett. 2003, 5: 4987

16 Suwa T. Sugiyama E. Shibata I. Baba A. Synthesis 2000, 789

17 Baelen GV. Maes BUW. Tetrahedron 2008, 64: 5604

18 Zhu LB. Guo P. Li GC. Lan JB. Xie RG. You JS. J. Org. Chem. 2007, 72: 8535