Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2006(11): 1868-1872
DOI: 10.1055/s-2006-942369
DOI: 10.1055/s-2006-942369
PAPER
© Georg Thieme Verlag Stuttgart · New York
Active-Copper-Promoted Expeditious N-Arylations in Aqueous Media under Microwave Irradiation
Further Information
Received
12 December 2005
Publication Date:
05 May 2006 (online)
Publication History
Publication Date:
05 May 2006 (online)
Abstract
Active-copper-promoted mild and expeditious N-arylations of amines, amides, imides, and β-lactams with aryl halides under microwave irradiation conditions are reported. These reactions can be performed at 85-90 °C in aqueous media as well as under solvent-free conditions to give good yields. However, under solvent-free conditions, lower yields are obtained.
Key words
aqueous media - active copper - β-lactams - microwave - N-arylation - solvent-free
- 1
Ullmann F. Ber. Dtsch. Chem. Ges. 1903, 36: 2382 - 2
Lindley J. Tetrahedron 1984, 40: 1433 - 3
Hassan J.Sevignon M.Gozzi C.Schulz E.Lemairc M. Chem. Rev. 2002, 102: 1359 - 4
Hartwig JF. Angew. Chem. Int. Ed. 1998, 37: 2046 - 5
Yang BH.Buchwald SL. J. Organomet. Chem. 1999, 576: 125 - 6
Muci AR.Buchwald SL. Top. Curr. Chem. 2002, 219: 131 - 7
Oida S.Yashida A.Hayashi T.Naikayama E.Sato S.Okhi E. Tetrahedron Lett. 1980, 21: 619 - 8
McCombie SW.Ganguly AK.Girijavallabhan VM.Jeffrey PD.Lin S.Pinto P.McPhail AT. Tetrahedron Lett. 1981, 22: 3489 - 9
Joyeau R.Dugenet Y.Wakselman M. J. Chem. Soc., Chem. Commun. 1983, 431 - 10
Joyeau R.Yadav LDS.Wakselman M. J. Chem. Soc., Perkin Trans. 1 1987, 1899 - 11
Yamamoto T.Kurata Y. Chem. Ind. (London) 1981, 737 - 12
Yamamoto T.Kurata Y. Can. J. Chem. 1983, 61: 86 - 13
Varma RS. Green Chem. 1999, 1: 43 - 14
Perreux L.Loupy A. Tetrahedron 2001, 57: 9199 - 15
Lidstrom P.Tierney J.Wathey B.Westman J. Tetrahedron 2001, 57: 9225 - 16
Kappe CO. Angew. Chem. Int. Ed. 2004, 43: 6250 - 17
Strohmeier GA.Kappe CO. J. Comb. Chem. 2002, 4: 154 - 18
Alexandre FR.Domon L.Frere S.Testard A.Thiery V.Besson T. Mol. Diversity 2003, 7: 273 - 19
Varma RS. J. Heterocycl. Chem. 1999, 36: 1565 - 20
Larhed M.Moberg C.Hallberg A. Acc. Chem. Res. 2002, 35: 717 - 21
Hayes BL. In Microwave Technology Chemistry at the Speed of Light CEM Publishing; Mathews NC: 2002. p.29 - 22
Varma RS. In Microwave Technology Chemical Applications: Kirk-Othmer Encyclopedia of Chemical Technology 5th ed.: John Wiley & Sons; New York: 2004. - 23
Li J.Chan TH. Organic Reaction in Aqueous Media John Wiley & Sons; New York: 1997. - 24
Grieco AP. Organic Synthesis in Water Blackie Academic and Professional; London: 1998. - 25
Kobayashi S.Manabe K. Acc. Chem. Res. 2002, 35: 209 - 26
Wei W.Keh CCK.Li CJ.Varma RS. Clean Tech. Environ. Policy 2005, 7: 62 - 27
Lindstrom UM. Chem. Rev. 2002, 102: 2751 - 28
An J.Bagnell L.Cablewski T.Strauss CR.Trainor RW. J. Org. Chem. 1997, 62: 2505 - 29
Strauss CR. Aust. J. Chem. 1999, 52: 83 - 30
Ju Y.Varma RS. Green Chem. 2004, 6: 219 - 31
Dandia A.Arya K.Sati M. Synth. Commun. 2004, 34: 1141 - 32
Ju Y.Varma RS. Org. Lett. 2005, 7: 2409 - 33
Yadav LDS.Kapoor R. J. Org. Chem. 2004, 69: 8118 - 34
Yadav LDS.Singh A. Tetrahedron Lett. 2003, 44: 5667 - 35
Yadav LDS.Singh S. Synthesis 2003, 63 - 36
Yadav LDS.Yadav S.Rai VK. Tetrahedron 2005, 61: 10013 - 37
Gore PH.Hughes GK. J. Chem. Soc. 1959, 1615