Palladium-Catalyzed Amination of Aryl Bromides Using Temperature-Controlled Microwave Heating

Yiqian  Wan; Mathias  Alterman; Anders  Hallberg

doi:10.1055/s-2002-33342

SPECIALTOPIC

Palladium-Catalyzed Amination of Aryl Bromides Using Temperature-
Controlled Microwave Heating

Yiqian Wan, Mathias Alterman*, Anders Hallberg
Department of Organic Pharmaceutical Chemistry, BMC, Uppsala University, P.O. Box 574, 75123 Uppsala, Sweden
e-Mail: mathias.alterman@orgfarm.uu.se;

Abstract

All articles of this category

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

Full Text

References

<A NAME="RC01602SS-1A">1a</A> Guram AS. Buchwald SL. J. Am. Chem. Soc. 1994, 116: 7901

<A NAME="RC01602SS-1B">1b</A> Paul F. Patt J. Hartwig JF. J. Am. Chem. Soc. 1994, 116: 5969

<A NAME="RC01602SS-2A">2a</A> Yang BH. Buchwald SL. J. Organomet. Chem. 1999, 576: 125

<A NAME="RC01602SS-2B">2b</A> Hartwig JF. Acc. Chem. Res. 1998, 31: 852

<A NAME="RC01602SS-2C">2c</A> Wolfe JP. Wagaw S. Marcoux J.-F. Buchwald SL. Acc. Chem. Res. 1998, 31: 805

<A NAME="RC01602SS-2D">2d</A> Hartwig JF. Angew. Chem. Int. Ed. 1998, 37: 2046

<A NAME="RC01602SS-3">3</A> Gribble GW. Lord PD. Skotnicki J. Dietz SE. Eaton JT. Johnson J. J. Am. Chem. Soc. 1974, 96: 7812

<A NAME="RC01602SS-4">4</A> ten Hoeve W. Kruse CG. Luteyn JM. Thiecke JRG. Wynberg H. J. Org. Chem. 1993, 58: 5101

<A NAME="RC01602SS-5A">5a</A> Kwong FY. Klapars A. Buchwald SL. Org. Lett. 2002, 4: 581

<A NAME="RC01602SS-5B">5b</A> Kiyomori A. Marcoux JF. Buchwald SL. Tetrahedron Lett. 1999, 40: 2657

<A NAME="RC01602SS-5C">5c</A> Lindley J. Tetrahedron 1984, 40: 1433

<A NAME="RC01602SS-6">6</A> Razzuk A. Biehl ER. J. Org. Chem. 1987, 52: 2619

<A NAME="RC01602SS-7">7</A> March J. Advanced Organic Chemistry 4th ed.: Wiley; New York: 1992.

<A NAME="RC01602SS-8A">8a</A> Grasa GA. Viciu MS. Huang JK. Nolan SP. J. Org. Chem. 2001, 66: 7729

<A NAME="RC01602SS-8B">8b</A> Ali MH. Buchwald SL. J. Org. Chem. 2001, 66: 2560

<A NAME="RC01602SS-9A">9a</A> Larhed M. Hallberg A. Drug Discovery Today 2001, 6: 406

<A NAME="RC01602SS-9B">9b</A> Larhed M. Hallberg A. J. Org. Chem. 1996, 61: 9582

<A NAME="RC01602SS-9C">9c</A> Alterman M. Hallberg A. J. Org. Chem. 2000, 65: 7984

<A NAME="RC01602SS-10">10</A> Sharifi A. Hosseinzadeh R. Mirzaei M. Monatsh. Chem. 2002, 133: 329

<A NAME="RC01602SS-11">11</A> Gabriel C. Gabriel S. Grant EH. Halstead BSJ. Mingos DMP. Chem. Soc. Rev. 1998, 27: 213

<A NAME="RC01602SS-12">12</A> 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

<A NAME="RC01602SS-13">13</A> 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

<A NAME="RC01602SS-14">14</A> Low C.-M. Ulgen M. Gorrod JW. J. Pharm. Pharmacol. 1994, 46: 585

<A NAME="RC01602SS-15A">15a</A> Lopez RM. Fu GC. Tetrahedron 1997, 53: 16349

<A NAME="RC01602SS-15B">15b</A> Tafel J. Pfeffermann E. Ber. Dtsch. Chem. Ges. 1902, 35: 1510

<A NAME="RC01602SS-16A">16a</A> Kanie K. Mizuno K. Kuroboshi M. Hiyama T. Bull. Chem. Soc. Jpn. 1998, 71: 1973

<A NAME="RC01602SS-16B">16b</A> Watanabe Y. Tsuji Y. Ige H. Ohsugi Y. Ohta T. J. Org. Chem. 1984, 49: 3359

<A NAME="RC01602SS-17">17</A> Bader H. Hansen AR. McCarty FJ. J. Org. Chem. 1966, 31: 2319

<A NAME="RC01602SS-18A">18a</A> Wolfe JP. Tomori H. Sadighi JP. Yin J. Buchwald SL. J. Org. Chem. 2000, 65: 1158

<A NAME="RC01602SS-18B">18b</A> Tsuji Y. Huh KT. Ohsugi Y. Watanabe Y. J. Org. Chem. 1985, 50: 1365

<A NAME="RC01602SS-19">19</A> Brenner E. Schneider R. Fort Y. Tetrahedron 1999, 55: 12829

<A NAME="RC01602SS-20">20</A> Suhr H. Grube H. Ber. Bunsen-Ges. Phys. Chem. 1966, 70: 544

<A NAME="RC01602SS-21A">21a</A> Wolfe JP. Buchwald SL. J. Org. Chem. 1997, 62: 6066

<A NAME="RC01602SS-21B">21b</A> Schnabel WJ. Raetz R. Kober E. J. Org. Chem. 1962, 27: 2514

<A NAME="RC01602SS-22A">22a</A> Katritzky AR. Cozens AJ. J. Chem. Soc., Perkin Trans. 1 1983, 2611

<A NAME="RC01602SS-22B">22b</A> Merz V. Weith W. Ber. Dtsch. Chem. Ges. 1873, 6: 1511

<A NAME="RC01602SS-23A">23a</A> Takeuchi H. Taniguchi T. Ueda T. J. Chem. Soc., Perkin Trans. 2 2000, 295

<A NAME="RC01602SS-23B">23b</A> Yamamura T. Suzuki K. Yamaguchi T. Nishiyama T. Bull. Chem. Soc. Jpn. 1997, 70: 413

<A NAME="RC01602SS-24">24</A> Takeuchi H. Takano K. J. Chem. Soc., Perkin Trans. 1 1986, 611

<A NAME="RC01602SS-25">25</A> Brenner E. Schneider R. Fort Y. Tetrahedron Lett. 2000, 41: 2881

<A NAME="RC01602SS-26">26</A> Khan MA. Polya JB. J. Chem. Soc. C 1970, 85