Pd-catalyzed O-arylation of ethyl acetohydroximate: Synthesis of O-arylhydroxylamines and substituted benzofurans

Journal of the American Chemical Society

Volumn 132, Issue 29, 2010, Pages 9990-9991

  Maimone, Thomas J ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL CHLORIDE; ARYL HALIDES; ARYLATIONS; BENZOFURANS; CROSS-COUPLINGS; PD CATALYST; SHORT REACTION TIME; SINGLE-STEP;

AROMATIC COMPOUNDS; BROMINE COMPOUNDS; CHLORINE COMPOUNDS; PALLADIUM; SYNTHESIS (CHEMICAL);

REACTION KINETICS;

BENZOFURAN DERIVATIVE; HYDROXYLAMINE; LIGAND; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; SYNTHESIS;

AMINES; BENZOFURANS; CATALYSIS; HYDROXAMIC ACIDS; PALLADIUM;

EID: 77955828931     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1044874     Document Type: Article

References (27)

1. Johnson, S. M.; Petrassi, H. M.; Palaninathan, S. K.; Mohamedmohaideen, N. N.; Purkey, H. E.; Nichols, C.; Chiang, K. P.; Walkup, T.; Sacchettini, J. C.; Sharpless, K. B.; Kelly, J. W. J. Med. Chem. 2005, 48, 1576.
2. Nazarpack-Kandlousy, N.; Chernushevich, I. V.; Meng, L.; Yang, Y.; Eliseev, A. V. J. Am. Chem. Soc. 2000, 122, 3358.
3. (a) Sheradsky, T. Tetrahedron Lett. 1966, 7, 5225.
4. (b) Castellino, A. J.; Rapoport, H. J. Org. Chem. 1984, 49, 4399.
5. (c) Takeda, N.; Miyata, O.; Naito, T. Eur. J. Org. Chem 2007, 1491.
6. (a) Miyazawa, E.; Sakamoto, T.; Kikugawa, Y Org. Prep. Proced. Int. 1997, 29, 594.
7. (b) Cadogan, J. I. G.; Rowley, A. G. Synth. Commun. 1977, 7, 365.
8. (c) Baldoni, C.; Del Bettero, P.; Licandro, E.; Maiorana, S. Synthesis 1988, 344.
9. (a) Castellino, A. J.; Rapoport, H. J. Org. Chem. 1984, 49, 1348.
10. (b) Tamura, Y.; Minamikawa, J.; Sumoto, K.; Fujii, S.; Ikeda, M. Synthesis 1977, 1.
11. (c) Foot, O. F.; Knight, D. W. Chem. Commun. 2000, 975.
12. Prithwiraj, D.; Nonappa.; Pandurangan, K.; Maitra, U.; Wailes, S. Org. Lett. 2007, 9, 2767.
13. (a) Feng, X.-H.; Zhang, G.-Z.; Chen, C.-Q.; Yang, M.-Y.; Xu, X.-Y.; Huang, G.-S. Synth. Commun. 2009, 39, 1768.
14. (b) Abdelselam, A.; Meyer, A. G.; Tuck, K. L. Synlett 2009, 955.
15. A polymer supported Cu-catalyst has also been shown to couple oximes with aryl boronic acids, see Wang, L.; Huang, C.; Cai, C. Catalysis Comm. 2010, 11, 532.
16. Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139.
17. For use of 1 see: (a) Fors, B. P.; Dooleweerdt, K.; Zeng, Q.; Buchwald, S. L. Tetrahedron 2009, 65, 6576.
18. (b) Watson, D. A.; Su, M.; Teverovskiy, G.; Zhang, Y.; Garcia-Fortanet, J.; Kinzel, T.; Buchwald, S. L. Science 2009, 325, 1661.
19. (c) Fors, B. P.; Buchwald, S. L. J. Am. Chem Soc. 2009, 131, 12898.
20. (a) Vorogushin, A. V.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 8146.
21. (b) Burgos, C. H.; Barder, T. E.; Huang, X.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 4321.
22. Blake, J. A.; Pratt, D. A.; Lin, S.; Walton, J. C.; Mulder, P.; Ingold, K. U. J. Org. Chem. 2004, 69, 3112.
23. For many examples of oxidative addition of Pd (0) into polarized oxime N-O bonds see: Narasaka, K.; Kitamura, M. Eur. J. Org. Chem. 2005, 4505.
24. We have observed the following trend in rate of C-O coupling: PhBr > PhI > PhCl.
25. 2.
26. (a) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6621.
27. (b) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251.