Copper-Catalyzed N-Arylation of Amines/Amides in Poly(ethylene glycol) as Recyclable Solvent Medium

Srivari Chandrasekhar; S. Shameem Sultana; Srinivasa Rao Yaragorla; N. Ramakrishna Reddy

doi:10.1055/s-2006-926328

PAPER

Copper-Catalyzed N-Arylation of Amines/Amides in Poly(ethylene glycol) as Recyclable Solvent Medium

Srivari Chandrasekhar*, S. Shameem Sultana, Srinivasa Rao Yaragorla, N. Ramakrishna Reddy
Organic division-1, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: srivaric@iict.res.in;

Abstract

All articles of this category

Abstract

The Buchwald N-arylation of amines and amides is achieved efficiently in PEG (400 Daltons) as solvent medium. The solvent and catalyst recyclability is studied. Interestingly amides underwent N-arylation with better yields.

Key words

N-arylation - copper iodide - poly(ethylene glycol) - reusability

Full Text

References

1a Craig PN. Comprehensive Medicinal Chemistry Vol. 8: Drayton CJ. Pergamon; New York: 1991.

1b Southon IW. Buckingham J. In Dictionary of Alkaloids Saxton JE. Chapman & Hall; London: 1989.

1c Negwer M. In Organic-Chemical Drugs and their Synonyms (An International Survey) 7th ed.: Akademie Verlag GmbH; Berlin: 1994.

2 Buckingham J. Dictionary of Natural Products-I University Press; Cambridge, MA: 1994.

3a Scott JD. Williams RM. Chem. Rev. 2004, 102: 1669

3b Chrzanowska M. Rozwadowska MD. Chem. Rev. 2004, 104: 3341

4 Yang BH. Buchwald SL. J. Organomet. Chem. 1999, 576: 125 ; and references cited therein

5a Harbert CA. Plattner JJ. Welch WM. Weissman A. Koe BK. J. Med. Chem. 1980, 23: 635

5b Lexy H. Kauffmann T. Chem. Ber. 1980, 113: 2755

5c Unanast PC. Connor DT. Stabler SR. Weikert RJ. J. Heterocycl. Chem. 1987, 24: 811

5d Kato Y. Conn MM. Rebek J. J. Am. Chem. Soc. 1994, 116: 3279

5e Murakami Y. Watnabe T. Hagiwara T. Akiyama T. Ishii H. Chem. Pharm. Bull. 1995, 43: 1281

5f Mederski WWKR. Lefort M. German M. Kux D. Tetrahedron 1999, 55: 2757

5g Collman JP. Zhong M. Org. Lett. 2000, 2: 1233

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

7 Chandrasekhar S. Narsihmulu Ch. Sultana SS. Reddy NR. Org. Lett. 2002, 4: 4399

8 Chandrasekhar S. Narsihmulu Ch. Sultana SS. Reddy NR. Chem. Commun. 2003, 1716

9a Chandrasekhar S. Narsihmulu Ch. Reddy NR. Sultana SS. Tetrahedron Lett. 2004, 45: 4581

9b Chandrasekhar S. Narsihmulu Ch. Reddy NR. Sultana SS. Chem. Commun. 2004, 2450

10a Chandrasekhar S. Narsihmulu Ch. Chandrasekhar G. Shyamsunder T. Tetrahedron Lett. 2004, 45: 2421

10b Chandrasekhar S. Shyamsunder T. Chandrasekhar G. Narsihmulu Ch. Synlett 2004, 522