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Synthesis 2002(11): 1597-1600
DOI: 10.1055/s-2002-33342
DOI: 10.1055/s-2002-33342
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York
Palladium-Catalyzed Amination
of Aryl Bromides Using Temperature-
Controlled Microwave
Heating
Further Information
Received
19 May 2002
Publication Date:
23 August 2002 (online)
Publication History
Publication Date:
23 August 2002 (online)
Abstract
Fast Palladium-catalyzed aminations of aryl bromides have been conducted in a non-inert reaction medium with temperature-controlled microwave heating. With a reaction time of 4 minutes at 130 °C or 180 °C, both electron-rich and electron-deficient aryl bromides reacted with various amines to provide fair to good yields of the corresponding secondary and tertiary anilines. As an example the amination of 4-bromobenzonitrile with imidazole is presented.
Key words
aminations - palladium - synthesis - catalysis - coupling
-
1a
Guram AS.Buchwald SL. J. Am. Chem. Soc. 1994, 116: 7901 -
1b
Paul F.Patt J.Hartwig JF. J. Am. Chem. Soc. 1994, 116: 5969 -
2a
Yang BH.Buchwald SL. J. Organomet. Chem. 1999, 576: 125 -
2b
Hartwig JF. Acc. Chem. Res. 1998, 31: 852 -
2c
Wolfe JP.Wagaw S.Marcoux J.-F.Buchwald SL. Acc. Chem. Res. 1998, 31: 805 -
2d
Hartwig JF. Angew. Chem. Int. Ed. 1998, 37: 2046 - 3
Gribble GW.Lord PD.Skotnicki J.Dietz SE.Eaton JT.Johnson J. J. Am. Chem. Soc. 1974, 96: 7812 - 4
ten Hoeve W.Kruse CG.Luteyn JM.Thiecke JRG.Wynberg H. J. Org. Chem. 1993, 58: 5101 -
5a
Kwong FY.Klapars A.Buchwald SL. Org. Lett. 2002, 4: 581 -
5b
Kiyomori A.Marcoux JF.Buchwald SL. Tetrahedron Lett. 1999, 40: 2657 -
5c
Lindley J. Tetrahedron 1984, 40: 1433 - 6
Razzuk A.Biehl ER. J. Org. Chem. 1987, 52: 2619 - 7
March J. Advanced Organic Chemistry 4th ed.: Wiley; New York: 1992. -
8a
Grasa GA.Viciu MS.Huang JK.Nolan SP. J. Org. Chem. 2001, 66: 7729 -
8b
Ali MH.Buchwald SL. J. Org. Chem. 2001, 66: 2560 -
9a
Larhed M.Hallberg A. Drug Discovery Today 2001, 6: 406 -
9b
Larhed M.Hallberg A. J. Org. Chem. 1996, 61: 9582 -
9c
Alterman M.Hallberg A. J. Org. Chem. 2000, 65: 7984 - 10
Sharifi A.Hosseinzadeh R.Mirzaei M. Monatsh. Chem. 2002, 133: 329 - 11
Gabriel C.Gabriel S.Grant EH.Halstead BSJ.Mingos DMP. Chem. Soc. Rev. 1998, 27: 213 - 12
Manetti D.Bartolini A.Borea PA.Bellucci C.Dei S.Ghelardini C.Gualtieri F.Romanelli MN.Scapecchi S.Teodori E.Varani K. Bioorg. Med. Chem. 1999, 7: 457 - 13
Alterman M.Andersson HO.Garg N.Ahlsen G.Lovgren S.Classon B.Danielson UH.Kvarnstrom I.Vrang L.Unge T.Samuelsson B.Hallberg A. J. Med. Chem. 1999, 42: 3835 - 14
Low C.-M.Ulgen M.Gorrod JW. J. Pharm. Pharmacol. 1994, 46: 585 -
15a
Lopez RM.Fu GC. Tetrahedron 1997, 53: 16349 -
15b
Tafel J.Pfeffermann E. Ber. Dtsch. Chem. Ges. 1902, 35: 1510 -
16a
Kanie K.Mizuno K.Kuroboshi M.Hiyama T. Bull. Chem. Soc. Jpn. 1998, 71: 1973 -
16b
Watanabe Y.Tsuji Y.Ige H.Ohsugi Y.Ohta T. J. Org. Chem. 1984, 49: 3359 - 17
Bader H.Hansen AR.McCarty FJ. J. Org. Chem. 1966, 31: 2319 -
18a
Wolfe JP.Tomori H.Sadighi JP.Yin J.Buchwald SL. J. Org. Chem. 2000, 65: 1158 -
18b
Tsuji Y.Huh KT.Ohsugi Y.Watanabe Y. J. Org. Chem. 1985, 50: 1365 - 19
Brenner E.Schneider R.Fort Y. Tetrahedron 1999, 55: 12829 - 20
Suhr H.Grube H. Ber. Bunsen-Ges. Phys. Chem. 1966, 70: 544 -
21a
Wolfe JP.Buchwald SL. J. Org. Chem. 1997, 62: 6066 -
21b
Schnabel WJ.Raetz R.Kober E. J. Org. Chem. 1962, 27: 2514 -
22a
Katritzky AR.Cozens AJ. J. Chem. Soc., Perkin Trans. 1 1983, 2611 -
22b
Merz V.Weith W. Ber. Dtsch. Chem. Ges. 1873, 6: 1511 -
23a
Takeuchi H.Taniguchi T.Ueda T. J. Chem. Soc., Perkin Trans. 2 2000, 295 -
23b
Yamamura T.Suzuki K.Yamaguchi T.Nishiyama T. Bull. Chem. Soc. Jpn. 1997, 70: 413 - 24
Takeuchi H.Takano K. J. Chem. Soc., Perkin Trans. 1 1986, 611 - 25
Brenner E.Schneider R.Fort Y. Tetrahedron Lett. 2000, 41: 2881 - 26
Khan MA.Polya JB. J. Chem. Soc. C 1970, 85