Pd-Catalyzed ortho-Arylation
of N-Aryloxazolidinones with Simple Arenes Using
Sodium Persulfate

Charles S. Yeung; Vy M. Dong

doi:10.1055/s-0030-1259731

LETTER

Pd-Catalyzed ortho-Arylation of N-Aryloxazolidinones with Simple Arenes Using Sodium Persulfate

Charles S. Yeung, Vy M. Dong*
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6, Canada
e-Mail: vdong@chem.utoronto.ca;

Abstract

Alle Artikel dieser Rubrik

Abstract

We report a Pd-catalyzed ortho-arylation of N-aryloxazolidinones under mild conditions. Our oxidative cross-coupling consumes sodium persulfate (Na₂S₂O₈), a green and environmentally benign reagent, as the terminal oxidant. Trifluoroacetic acid (TFA) is critical for reactivity.

Key words

palladium - arylation - biaryl - cross-coupling - metallacycle

Volltext

Referenzen

References

For a review of the therapeutic properties of N-aryloxazo-lidinones, see:

1a Halle E. Majcher-Peszynska J. Drewelow B. Chemother. J. 2002, 11: 1

For selected examples, see:

1b Genin MJ. Hutchinson DK. Allwine DA. Hester JB. Emmert DE. Garmon SA. Ford CW. Zurenko GE. Hamel JC. Schaadt RD. Stapert D. Yagi BH. Friis JM. Shobe EM. Adams WJ. J. Med. Chem. 1998, 41: 5144

1c Tucker JA. Allwine DA. Grega KC. Barbachyn MR. Klock JL. Adamski JL. Brickner SJ. Hutchinson DK. Ford CW. Zurenko GE. Conradi RA. Burton PSM. J. Med. Chem. 1998, 41: 3727

1d Gleave DM. Brickner SJ. Manninen PR. Allwine DA. Lovasz KD. Rohrer DC. Tucker JA. Zurenko GE. Ford CW. Bioorg. Med. Chem. Lett. 1998, 8: 1231

1e Moureau F. Wouters J. Vercauteren DP. Collin S. Evrard G. Durant F. Ducrey F. Koenig JJ. Jarreau FX. Eur. J. Med. Chem. 1994, 269

1f Moureau F. Wouters J. Vercauteren DP. Collin S. Evrard G. Durant F. Ducrey F. Koenig JJ. Jarreau FX. Eur.
J. Med. Chem. 1992, 939

For selected examples, see:

2a Aroua L. Baklouti A. Synth. Commun. 2007, 37: 1935

2b Ghosh A. Sieser JE. Caron S. Couturier M. Dupont-Gaudet K. Girardin M. J. Org. Chem. 2006, 71: 1258

2c Griera R. Cantos-Llopart C. Amat M. Bosch J. de Castillo J.-C. Huguet J. Bioorg. Med. Chem. Lett. 2005, 15: 2515

2d Ghosh A. Sieser JE. Riou M. Cai W. Rivera-Ruiz L. Org. Lett. 2003, 5: 2207

2e Cacchi S. Fabrizi G. Goggiamani A. Heterocycles 2003, 61: 505

2f Gleave DM. Brickner SJ. Manninen PR. Allwine DA. Lovasz KD. Rohrer DC. Tucker JA. Zurenko GE. Ford CW. Bioorg. Med. Chem. Lett. 1998, 8: 1231

2g Gleave DM. Brickner SJ. J. Org. Chem. 1996, 61: 6470

For selected reviews, see:

3a Lyons TW. Sanford MS. Chem. Rev. 2010, 110: 1147

3b Colby DA. Bergman RG. Ellman JA. Chem. Rev. 2010, 110: 624

3c Daugulis O. Zaitsev VG. Shabashov D. Pham Q.-N. Lazareva A. Synlett 2006, 3382

3d Ritleng V. Sirlin C. Pfeffer M. Chem. Rev. 2002, 102: 1731

3e Chen X. Engle K. Wang D.-H. Yu J.-Q. Angew. Chem. Int. Ed. 2009, 48: 5094

3f Dupont J. Consorti CS. Spencer J. Chem. Rev. 2005, 105: 2527

3g Shilov AE. Shul’pin GB. Chem. Rev. 1997, 97: 2879

3h Ryabov AD. Chem. Rev. 1990, 90: 403

4a Kalyani D. Deprez NR. Desai LV. Sanford MS. J. Am. Chem. Soc. 2005, 127: 7330

For a related Boc-directed C-H bond functionalization, see:

4b Wang D.-H. Hao X.-S. Wu D.-F. Yu JQ. Org. Lett. 2006, 8: 3387

For related O-carbamate directed C-H bond functionalizations, see:

4c Zhao X. Yeung CS. Dong VM. J. Am. Chem. Soc. 2010, 132: 5837

4d Bedford RB. Webster RL. Mitchell CJ. Org. Biomol. Chem. 2009, 7: 4853

4e Xiao B. Fu Y. Xu J. Gong T.-J. Dai J.-J. Yi J. Liu L. J. Am. Chem. Soc. 2010, 132: 468

For selected reviews, see:

5a Corbet J.-P. Mignani G. Chem. Rev. 2006, 106: 2651

5b Hassan J. Sévignon M. Gozzi C. Schulz E. Lemaire M. Chem. Rev. 2002, 102: 1359

For selected reviews, see:

6a McGlacken GP. Batemann LM. Chem. Soc. Rev. 2009, 38: 2447

6b Ashenhurst JA. Chem. Soc. Rev. 2010, 39: 540

6c Li B.-J. Yang S.-D. Shi Z.-J. Synlett 2008, 949

6d Ackermann L. Vicente R. Kapdi A. Angew. Chem. Int. Ed. 2009, 48: 9792

For selected examples, see:

6e Stuart DR. Fagnou K. Science 2007, 316: 1172

6f Stuart DR. Villemure E. Fagnou K. J. Am. Chem. Soc. 2007, 129: 12072

6g Hull KL. Sanford MS. J. Am. Chem. Soc. 2007, 129: 11904

6h Hull KL. Sanford MS. J. Am. Chem. Soc. 2009, 131: 9651

6i Yeung CS. Zhao X. Borduas N. Dong VM. Chem. Sci. 2010, 1: 331

6j Li B.-J. Tian S.-L. Fang Z. Shi Z.-J. Angew. Chem. Int. Ed. 2008, 47: 1115

6k Brasche G. Garcia-Fortanet J. Buchwald SL. Org. Lett. 2008, 10: 2207

6l Xia J.-B. You S.-L. Organometallics 2007, 26: 4869

6m Cho SH. Hwang SJ. Chang S. J. Am. Chem. Soc. 2008, 130: 9254

6n Dwight TA. Rue NR. Charyk D. Josselyn R. DeBoef B. Org. Lett. 2007, 9: 3137

6o Potavathri S. Dumas AS. Dwight TA. Naumiec GR. Hammann JM. DeBoef B. Tetrahedron Lett. 2008, 49: 4050

6p Li R. Jiang L. Lu W. Organometallics 2006, 25: 5973

Zusatzmaterial

Supporting Information