A convenient and general method for Pd-catalyzed Suzuki cross-couplings of aryl chlorides and arylboronic acids

Angewandte Chemie - International Edition

Volumn 37, Issue 24, 1999, Pages 3387-3388

  Littke, Adam F ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Cross coupling; Homogenous catalysis; Palladium; Suzuki reaction

Indexed keywords

BORONIC ACID DERIVATIVE; CHLORIDE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; METHODOLOGY;

EID: 0033521580     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981231)37:24<3387::AID-ANIE3387>3.0.CO;2-P     Document Type: Article

References (31)

1. For a review, see N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
2. For a review, see V. Farina, V. Krishnamurthy, W. J. Scott, Org. React. 1997, 50, 1-652.
3. For discussions of the toxicity of triorganotin compounds, see a) S. J. De Mora, Tributyltin: Case Study of an Environmental Contaminant, Cambridge University Press, Cambridge, 1996, b) I. J. Boyer, Toxicology 1989, 55, 253-298.
4. For discussions of the toxicity of triorganotin compounds, see a) S. J. De Mora, Tributyltin: Case Study of an Environmental Contaminant, Cambridge University Press, Cambridge, 1996, b) I. J. Boyer, Toxicology 1989, 55, 253-298.
5. 0 more readily than do the corresponding unsubstituted aryl halides. For discussions, see a) V. V. Grushin, H. Alper, Chem. Rev. 1994, 94, 1047-1062; b) references [1, 2].
6. a) S. Gronowitz, A.-B. Hörnfeldt, V. Kristjansson, T. Musil, Chem. Scr. 1986, 26, 305-309;
7. b) W. J. Thompson, J. H. Jones, P. A. Lyle, J. E. Thies, J. Org. Chem. 1988, 53, 2052-2055;
8. c) M. B. Mitchell, P. J. Wallbank, Tetrahedron Lett. 1991, 32, 2273-2276;
9. d) M. Uemura, H. Nishimura, K. Kamikawa, K. Nakayama, Y. Hayashi, Tetrahedron Lett. 1994, 35, 1909-1912;
10. e) M. Beller, H. Fischer, W. A. Hermann, K. Ofele, C. Brossmer, Angew. Chem. 1995, 107, 1992-1993; Angew. Chem. Int. Ed. Engl. 1995, 34, 1848-1849;
11. e) M. Beller, H. Fischer, W. A. Hermann, K. Ofele, C. Brossmer, Angew. Chem. 1995, 107, 1992-1993; Angew. Chem. Int. Ed. Engl. 1995, 34, 1848-1849;
12. f) S. Saito, M. Sakai, N. Miyaura, Tetrahedron Lett. 1996, 37, 2993-2996;
13. g) W. Shen, Tetrahedron Lett. 1997, 38, 5575-5578;
14. h) W. A. Herrmann, C.-P. Reisinger, M. Spiegler, J. Organomet. Chem. 1998, 557, 93-96;
15. i) F. Firooznia, C. Gude, K. Chan, Y. Satoh, Tetrahedron Lett. 1998, 39, 3985-3988.
16. For nickel-catalyzed cross-couplings of aryl chlorides and arylboronic acids, see a) S. Saito, S. Oh-tani, N. Miyaura, J. Org. Chem. 1997, 62, 8024-8030; b) A. F. Indolese, Tetrahedron Lett. 1997, 38, 3513-3516; c) reference [5i].
17. For nickel-catalyzed cross-couplings of aryl chlorides and arylboronic acids, see a) S. Saito, S. Oh-tani, N. Miyaura, J. Org. Chem. 1997, 62, 8024-8030; b) A. F. Indolese, Tetrahedron Lett. 1997, 38, 3513-3516; c) reference [5i].
18. 3 is used as a ligand, see M. Nishiyama, T. Yamamoto, Y. Koie, Tetrahedron Lett. 1998, 39, 617-620; T. Yamamoto, M. Nishiyama, Y. Koie, Tetrahedron Lett. 1998, 39, 2367-2370;
19. 3 is used as a ligand, see M. Nishiyama, T. Yamamoto, Y. Koie, Tetrahedron Lett. 1998, 39, 617-620; T. Yamamoto, M. Nishiyama, Y. Koie, Tetrahedron Lett. 1998, 39, 2367-2370;
20. b) For other reports that deal with the use of electron-rich phosphanes in palladium-catalyzed cross-couplings, see M. Portnoy, D. Milstein, Organometallics 1993, 12, 1655-1664; M. Portnoy, D. Milstein, Organometallics 1993, 12, 1665-1673; M. Portnoy, Y. Ben-David, D. Milstein, Organometallics 1993, 12, 4734-4735; N. P. Reddy, M. Tanaka, Tetrahedron Lett. 1997, 38, 4807-4810; reference [4a].
21. b) For other reports that deal with the use of electron-rich phosphanes in palladium-catalyzed cross-couplings, see M. Portnoy, D. Milstein, Organometallics 1993, 12, 1655-1664; M. Portnoy, D. Milstein, Organometallics 1993, 12, 1665-1673; M. Portnoy, Y. Ben-David, D. Milstein, Organometallics 1993, 12, 4734-4735; N. P. Reddy, M. Tanaka, Tetrahedron Lett. 1997, 38, 4807-4810; reference [4a].
22. b) For other reports that deal with the use of electron-rich phosphanes in palladium-catalyzed cross-couplings, see M. Portnoy, D. Milstein, Organometallics 1993, 12, 1655-1664; M. Portnoy, D. Milstein, Organometallics 1993, 12, 1665-1673; M. Portnoy, Y. Ben-David, D. Milstein, Organometallics 1993, 12, 4734-4735; N. P. Reddy, M. Tanaka, Tetrahedron Lett. 1997, 38, 4807-4810; reference [4a].
23. b) For other reports that deal with the use of electron-rich phosphanes in palladium-catalyzed cross-couplings, see M. Portnoy, D. Milstein, Organometallics 1993, 12, 1655-1664; M. Portnoy, D. Milstein, Organometallics 1993, 12, 1665-1673; M. Portnoy, Y. Ben-David, D. Milstein, Organometallics 1993, 12, 4734-4735; N. P. Reddy, M. Tanaka, Tetrahedron Lett. 1997, 38, 4807-4810; reference [4a].
24. 3 in Suzuki reactions, see H. E. Katz, J. Org. Chem. 1987, 52, 3932-3934; C. R. Johnson, M. P. Braun, J. Am. Chem. Soc. 1993, 115, 11014-11015;
25. 3 in Suzuki reactions, see H. E. Katz, J. Org. Chem. 1987, 52, 3932-3934; C. R. Johnson, M. P. Braun, J. Am. Chem. Soc. 1993, 115, 11014-11015;
26. 3 in other palladium-catalyzed cross-couplings, see J. P. Wolfe, S. L. Buchwald, Tetrahedron Lett. 1997, 38, 6359-6362; T. Satoh, Y. Kawamura, M. Miura, M. Nomura, Angew. Chem. 1997, 109, 1820-1822; Angew. Chem. Int. Ed. Engl. 1997, 36, 1740-1742.
27. 3 in other palladium-catalyzed cross-couplings, see J. P. Wolfe, S. L. Buchwald, Tetrahedron Lett. 1997, 38, 6359-6362; T. Satoh, Y. Kawamura, M. Miura, M. Nomura, Angew. Chem. 1997, 109, 1820-1822; Angew. Chem. Int. Ed. Engl. 1997, 36, 1740-1742.
28. 3 in other palladium-catalyzed cross-couplings, see J. P. Wolfe, S. L. Buchwald, Tetrahedron Lett. 1997, 38, 6359-6362; T. Satoh, Y. Kawamura, M. Miura, M. Nomura, Angew. Chem. 1997, 109, 1820-1822; Angew. Chem. Int. Ed. Engl. 1997, 36, 1740-1742.
29. Very recently we have found that CsF is also an extremely effective base.
30. 2O, filtered through a pad of Celite, concentrated, and purified by flash chromatography.
31. Note added in proof (November 2, 1998): Buchwald et al. have reported a versatile method for Suzuki cross-coupling of aryl chlorides: D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723.