Palladium-catalyzed C-O coupling involving unactivated aryl halides. Sterically induced reductive elimination to form the C-O bond in diaryl ethers [4]

Journal of the American Chemical Society

Volumn 121, Issue 13, 1999, Pages 3224-3225

  Mann, Grace ^b   Incarvito, Christopher ^a   Rheingold, Arnold L ^a   Hartwig, John F ^b  

^a YALE UNIVERSITY   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE; HALIDE; PALLADIUM;

CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; LETTER; LIGAND BINDING; STEREOCHEMISTRY; STOICHIOMETRY; X RAY DIFFRACTION;

EID: 0033531744     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984321a     Document Type: Letter

References (28)

1. Matsunaga, P. T.; Mavropoulos, J. C.; Hillhouse, G. L. Polyhedron 1995, 14, 175.
2. Koo, K.; Hillhouse, G. L.; Rheingold, A. L. Organometallics 1995, 14, 456.
3. Han, R.; Hillhouse, G. L. J. Am. Chem. Soc. 1997, 119, 8135.
4. Mann, G.; Hartwig, J. J. Am. Chem. Soc. 1996, 118, 13109.
5. Widenhoefer, R. A.; Zhong, H. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6787.
6. Widenhoefer, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6504.
7. Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937.
8. Marcoux, J. F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539.
9. Bigot, A.; Zhu, J. Tetrahedron Lett. 1998, 39, 551.
10. Pearson, A. J.; Bignan, G. Tetrahedron Lett. 1996, 37, 735.
11. Boger, D L.; Yohannes, D. J. Org. Chem. 1991, 56, 1763.
12. Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413.
13. Mann, G.; Hartwig, J. F. Tetrahedron Lett. 1997, 38, 8005.
14. Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 10333.
15. Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 3395.
16. Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369.
17. Mann, B. E.; Shaw, B. L.; Slade, R. M. J. Chem. Soc. A 1971, 2976.
18. Only a trace of the more common product from C-C bond formation was present in the isolated material.
19. 3, Z = 8, R(F) = 0.056, GOF = 1.83.
20. Meyer, U.; Werner, H. Chem. Rev. 1990, 123, 697.
21. 3 rule out this possibility.
22. Louie, J.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 11598.
23. Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 8232.
24. Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2.
25. Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1740.
26. Satoh, T.; Inoh, J.; Kawamura, Y.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 2239.
27. Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617.
28. Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367.