Novel Synthetic Strategy of N-Arylated Heterocycles via Sequential Palladium-Catalyzed Intra- and Inter-Arylamination Reactions

Rafik Omar-Amrani; Raphaël Schneider; Yves Fort

doi:10.1055/s-2004-831205

PAPER

Novel Synthetic Strategy of N-Arylated Heterocycles via Sequential Palladium-Catalyzed Intra- and Inter-Arylamination Reactions

Rafik Omar-Amrani, Raphaël Schneider*, Yves Fort*
Synthèse Organométallique et Réactivité, UMR CNRS-UHP 7565, Faculté des Sciences, BP 239, 54506 Vandoeuvre les Nancy Cedex, France
Fax: +33(3)83684785; e-Mail: Raphael.Schneider@sor.uhp-nancy.fr; Yves.Fort@sor.uhp-nancy.fr;

Abstract

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Abstract

The use of an in situ generated Pd(0) catalyst associated to N,N′-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene (SIPr) as a ligand and t-BuONa as the base for sequential intra- followed by intermolecular aryl amination is described. The method has been applied to the synthesis of N-arylated five-, six- and seven-membered nitrogen heterocycles.

Key words

palladium catalyst - N-heterocyclic carbene ligand - aryl amination reaction - N-arylated heterocycles

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References

1a Combs DW. Rampulla MS. Bell SC. Klaubert DH. Tobia AJ. Falotico R. Haertlein B. Lakas-Weiss C. Moore JB. J. Med. Chem. 1990, 33: 380

1b Stabler SR. ; Jahangir Synth. Commun. 1994, 24: 123

1c Andersen K. Liljefors T. Hyttel J. Perregaard J. J. Med. Chem. 1996, 39: 3723

1d Spadoni G. Balsamini C. Bedini A. Diamantini G. Giancomo BD. Tontini A. Tarzia G. J. Med. Chem. 1998, 41: 3624

1e Abramov IG. Smirnov AV. Kalandadza LS. Sakharov VN. Plakhtinskii VV. Heterocycles 2003, 60: 1611

For reviews, see:

2a Wolfe JP. Wagaw S. Marcoux J.-F. Buchwald SL. Acc. Chem. Res. 1998, 31: 805

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

2c Yang BH. Buchwald SL. J. Organomet. Chem. 1999, 576: 125

2d Muci AR. Buchwald SL. Practical Palladium Catalysts for C-N and C-O Bond Formation, In Cross-Coupling Reaction: A Practical Guide, Topics in Current Chemistry Ser. 219 Miyaura N. Springer-Verlag; New York: 2002.

3a Wolfe JP. Buchwald SL. J. Am. Chem. Soc. 1997, 119: 6054

3b Brenner E. Fort Y. Tetrahedron Lett. 1998, 39: 5359

3c Brenner E. Schneider R. Fort Y. Tetrahedron 1999, 55: 12829

3d Desmarets C. Schneider R. Fort Y. Tetrahedron Lett. 2000, 41: 2875

3e Brenner E. Schneider R. Fort Y. Tetrahedron Lett. 2000, 41: 288

3f Lipshutz BH. Ueda H. Angew. Chem. Int. Ed. 2000, 39: 4492

3g Desmarets C. Schneider R. Fort Y. Tetrahedron Lett. 2001, 42: 247

3h Desmarets C. Schneider R. Fort Y. Tetrahedron 2001, 57: 7657

3i Brenner E. Schneider R. Fort Y. Tetrahedron 2002, 58: 6913

3j Desmarets C. Schneider R. Fort Y. Walcarius A. J. Chem. Soc., Perkin Trans. 2 2002, 1844

3k Lipshutz BH. Tasler S. Chrisman W. Spliethoff B. Tesche B. J. Org. Chem. 2003, 68: 1177

3l Tasler S. Lipshutz BH. J. Org. Chem. 2003, 68: 1190

4a Wolfe JP. Rennels RA. Buchwald SL. Tetrahedron 1996, 52: 7525

4b Peat AJ. Buchwald SL. J. Am. Chem. Soc. 1996, 118: 1028

4c Wagaw S. Rennels RA. Buchwald SL. J. Am. Chem. Soc. 1997, 119: 8451

4d He F. Foxman BM. Snider BB. J. Am. Chem. Soc. 1998, 120: 6417

4e Abouabdellah A. Dodd RH. Tetrahedron Lett. 1998, 39: 2119

4f Yang BH. Buchwald SL. Org. Lett. 1999, 1: 35

4g Watanabe M. Yamamoto T. Nishiyama M. Angew. Chem. Int. Ed. 2000, 39: 2501

4h Brown JA. Tetrahedron Lett. 2000, 41: 1623

4i Song JJ. Yee NK. Org. Lett. 2000, 2: 519

4j Song JJ. Yee NK. Tetrahedron Lett. 2001, 42: 2937

4k Yu Y. Ostrech JM. Houghten RA. Tetrahedron Lett. 2003, 44: 2569

4l Qadir M. Priestley RE. Rising TWD. Gelbrich T. Coles SM. Hursthouse MB. Sheldrake PW. Whittall N. Hii KK. Tetrahedron Lett. 2003, 44: 3675

4m Brain CT. Steer JT. J. Org. Chem. 2003, 68: 6814

5a Hartwig JF. Kawatsura M. Hauck SI. Shaughnessy KH. Alcazar-Roman LM. J. Org. Chem. 1999, 64: 5575

5b Old DW. Harris MC. Buchwald SL. Org. Lett. 2000, 2: 1403

5c Meneyrol J. Helissey P. Tratrat C. Giorgi-Renault S. Husson H.-P. Synth. Commun. 2001, 31: 987

6a Beller M. Breindl C. Riermeier TH. Eichberger M. Trauthwein H. Angew. Chem. Int. Ed. 1998, 37: 3389

6b Beller M. Breindl C. Riermeier TH. Tillack A. J. Org. Chem. 2001, 66: 1403

7a Herrmann WA. Reisinger CP. Spiegler M. J. Organomet. Chem. 1998, 557: 93

7b Böhm VPW. Gstöttmayr CWK. Weskamp T. Herrmann WA. J. Organomet. Chem. 2000, 595: 186

7c Bourissou D. Guerret O. Gabbaï FP. Bertrand G. Chem. Rev. 2000, 100: 39

7d Herrmann WA. Angew. Chem. Int. Ed. 2002, 41: 1290

8a Gradel B. Brenner E. Schneider R. Fort Y. Tetrahedron Lett. 2001, 42: 5689

8b Desmarets C. Schneider R. Fort Y. J. Org. Chem. 2002, 67: 3029

9 Omar-Amrani R. Thomas A. Brenner E. Schneider R. Fort Y. Org. Lett. 2003, 5: 2311

10a Desmarets C. Kuhl S. Schneider R. Fort Y. Organometallics 2002, 21: 1554

10b Kuhl S. Schneider R. Fort Y. Adv. Synth. Catal. 2003, 345: 341

10c Kuhl S. Schneider R. Fort Y. Organometallics 2003, 22: 4184

11a Huang J. Grasa G. Nolan SP. Org. Lett. 1999, 1: 1307

11b Grasa GA. Viciu MS. Huang J. Nolan SP. J. Org. Chem. 2001, 66: 7729

11c Viciu MS. Kissling RM. Stevens ED. Nolan SP. Org. Lett. 2002, 4: 2229

11d Hillier AC. Grasa GA. Viciu MS. Lee HM. Yang C. Nolan SP. J. Organomet. Chem. 2002, 653: 69

11e Viciu MS. Kelly RA. Stevens ED. Naud F. Studer M. Nolan SP. Org. Lett. 2003, 5: 1479

11f Marion N. Navarro O. Kelly RA. Nolan SP. Synthesis 2003, 2590

12 Stauffer SR. Lee S. Stambuli JP. Hauck SI. Hartwig JF. Org. Lett. 2000, 2: 1423

13a Selvakumar K. Zapf A. Spannenberg M. Beller M. Chem.-Eur. J. 2002, 8: 3901

13b Selvakumar K. Zapf A. Beller M. Org. Lett. 2002, 4: 3031

13c Jackstell R. Frisch A. Beller M. Röttger D. Malaun M. Bildstein B. J. Mol. Catal. A: Chem. 2002, 185: 105

13d Frisch AC. Zapf A. Briel O. Kayser B. Shaikh N. Beller M. J. Mol. Cat. A: Chem. 2004, 214: 231

14a Böhm VPW. Weskamp T. Gstöttmayr CWK. Herrmann WA. Angew. Chem. Int. Ed. 2000, 39: 1602

14b Böhm VPW. Gstöttmayr CWK. Weskamp T. Herrmann WA. Angew. Chem. Int. Ed. 2001, 40: 3387

14c Herrmann WA. Olefe K. Von Preysing D. Schneider SK. J. Organomet. Chem. 2003, 687: 229

15

SIPr·HCl is commercially available from Strem Chemicals Inc.

16 Perrin DD. Amarego WLF. Purification of Laboratory Chemicals 3rd ed.: Pergamon; Oxford: 1998.