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

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Synthesis 2010(8): 1280-1284
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;

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Publication History

Received 27 October 2009
Publication Date:
05 February 2010 (online)

Abstract
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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

References

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

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

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

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

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

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

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

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

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

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

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

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

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

Google Scholar
3a Lindley J. Tetrahedron 1984, 40: 1433

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Crossref PubMed Google Scholar
12 Wang D. Ding K. Chem. Commun. 2009, 1891

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

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

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

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

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

Google Scholar
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

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

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

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

Article in Thieme Connect Google Scholar
17 Baelen GV. Maes BUW. Tetrahedron 2008, 64: 5604

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

Crossref Google Scholar