General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water

Angewandte Chemie - International Edition

Volumn 44, Issue 38, 2005, Pages 6173-6177

  Anderson, Kevin W ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Alkynes; Aryl chlorides; Boronic acids; Cross coupling; Water

Indexed keywords

ALKYNES; ARYL CHLORIDES; BORONIC ACIDS; CROSS-COUPLING;

CATALYSIS; CATALYSTS; CHLORINE COMPOUNDS; ORGANIC SOLVENTS; PALLADIUM COMPOUNDS; WATER;

PHOSPHORUS COMPOUNDS;

CHLORIDE; HALOGENATED HYDROCARBON; LIGAND; WATER;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

ANIMALS; CHLORIDES; HYDROCARBONS, HALOGENATED; LIGANDS; MOLECULAR STRUCTURE; WATER;

EID: 25844440760     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200502017     Document Type: Article

References (52)

1. Metal-Catalyzed Cross-Coupling Reactions, Vol. 2 (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004.
2. a) N. Miyaura, Top. Curr. Chem. 2002, 219, 11;
3. b) A. Suzuki, J. Organomet. Chem. 1999, 576, 147.
4. a) T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4685;
5. b) T. E. Barder, S. L. Buchwald, Org. Lett. 2004, 6, 2649;
6. c) S. D. Walker, T. E. Barder, J. R. Martinelli, S. L. Buchwald, Angew. Chem. 2004, 116, 1907;
7. Angew. Chem. Int. Ed. 2004, 43, 1871.
8. a) C.-J. Li, T.-H. Chan, Organic Reactions in Aqueous Media, Wiley, New York, 1997;
9. b) Organic Synthesis in Water (Ed.: P. A. Grieco), Academic Press, Dordrecht, The Netherlands, 1997;
10. c) Aqueous-Phase Organometallic Catalysis, 2nd ed. (Eds.: B. Cornils, W. A. Herrmann), Wiley-VCH, Weinheim, 2004;
11. d) K. H. Shaughnessy, R. B. DeVasher, Curr. Org. Chem. 2005, 9, 585;
12. e) N. E. Leadbeater, Chem. Commun. 2005, 2881.
13. 2/dppe/trisulfonated triphenylphosphine system, see: J.-C. Galland, M. Savignac, J. P. Genet, Tetrahedron Lett. 1999, 40, 2323.
14. For oxime-derived palladacycles, see: a) L. Botella, C. Najera, Angew. Chem. 2002, 114, 187;
15. Angew. Chem. Int. Ed. 2002, 41, 179;
16. b) L. Botella, C. Najera, J. Organomet. Chem. 2002, 663, 46.
17. For di-2-pyridylmethylamine-based palladium complexes, see: C. Najera, J. Gil-Molto, S. Karlstrom, L. R. Falvello, Org. Lett. 2003, 5, 1451.
18. For palladium N-heterocyclic carbene complexes, see: a) I. Ozdemir, Y. Gok, N. Gurbuz, E. Cetinkaya, B. Cetinkaya, Heteroat. Chem. 2004, 15, 419;
19. b) I. Özdemir, S. Demir, S. Yaser, B. Cetinkaya, Appl. Organomet. Chem. 2005, 19, 55.
20. For TBAB-water mixtures, see: R. B. Bedford, M. E. Blake, C. P. Butts, D. Holder, Chem. Commun. 2003, 466.
21. a) H. Gulyas, A. Szollosy, P. Szabo, P. Halmos, J. Bakos, Eur. J. Org. Chem. 2003, 2775;
22. b) W. P. Mul, K. Ramkisoensing, P. C. J. Kamer, J. N. H. Reek, A. J. van der Linder, A. Marson, P. W. N. M. van Leeuwen, Adv. Synth. Catal. 2002, 344, 293;
23. c) H. Gulyas, A. Szollosy, B. E. Hanson, J. Bakos, Tetrahedron Lett. 2002, 43, 2543;
24. d) E. Schwab, S. Mecking, Organometallics 2001, 20, 5504.
25. a) L. R. Moore, K. H. Shaughnessy, Org. Lett. 2004, 6, 225;
26. b) E. C. Western, J. R. Daft, E. M. Johnson II, P. M. Gannett, K. H. Shaughnessy, J. Org. Chem. 2003, 68, 6767;
27. c) A. E. Sollewijn Gelpke, J. J. N. Veerman, M. S. Goedheijt, P. C. J. Kamer, P. W. N. M. van Leeuwen, H. Hiemstra, Tetrahedron 1999, 55, 6657;
28. d) H. Bahrmann, K. Bergrath, H.-J. Kleiner, P. Lappe, C. Naumann, D. Peters, D. Regnat, J. Organomet. Chem. 1996, 520, 97;
29. e) J. P. Genet, A. Linquist, E. Blart, V. Mouries, M. Savignac, Tetrahedron Lett. 1995, 36, 1443.
30. a) R. B. DeVasher, L. R. Moore, K. H. Shaughnessy, J. Org. Chem. 2004, 69, 7919;
31. b) R. B. DeVasher, J. M. Spruell, D. A. Dixon, G. A. Broker, S. T. Griffin, R. D. Rogers, K. H. Shaughnessy, Organometallics 2005, 24, 962.
32. A. Konovets, A. Penciu, E. Framery, N. Percina, C. Goux-Henry, D. Sinou, Tetrahedron Lett. 2005, 46, 3205.
33. R. K. Arvela, N. E. Leadbeater, Org. Lett. 2005, 7, 2101.
34. For an excellent review on catalyst systems used in Suzuki-Miyaura couplings conducted in aqueous media and using microwave irradiation, see references [4d] and [4e], and references therein.
35. Our attempts to effect the coupling of 2-bromomesitylene with 2,6-dimethylphenylboronic acid in water at 100°C to form a biaryl with four substituents ortho to the aryl-aryl connection provided none of the desired product. This is in contrast to what is observed with a catalytic system using 1. See ref. [2c].
36. The sulfonic acid is undoubtedly rapidly transformed to the sulfonate under the reaction conditions. For examples of Suzuki-Miyaura couplings of aryl halides with protected sulfonic acids, see: a) B. G. Avitabile, C. A. Smith, D. B. Judd, Org. Lett. 2005, 7, 843;
37. b) A. Hari, B. L. Miller, Org. Lett. 1999, 1, 2109;
38. c) E. W. Baxter, J. K. Rueter, S. O. Nortey, A. B. Reitz, Tetrahedron Lett. 1998, 39, 979.
39. See references [4] and [10b].
40. The authors report that monodentate phosphines are poor ligands for the Suzuki-Miyaura coupling of 2-amino-pyridines and pyrimidines. This result suggests that use of a highly active catalyst system such as Pd/2 at least in some instances overcomes this limitation; see: T. Itoh, T. Mase, Tetrahedron Lett. 2005, 46, 3573.
41. D. Gelman, S. L. Buchwald, Angew. Chem. 2003, 115, 6175;
42. Angew. Chem. Int. Ed. 2003, 42, 5993.
43. For recent reports of Sonogashira coupling reactions conducted in water or water/organic biphasic solvents, see: a) B. Liang, M. Dai, J. Chen, Z. Yang, J. Org. Chem. 2005, 70, 391;
44. b) G. Zhang, Synlett 2005, 4, 619;
45. c) M. S. Mohamed Ahmed, A. Mori, Tetrahedron 2004, 60, 9977;
46. d) C. Wolf, R. Lerebours, Org. Biomol. Chem. 2004, 2, 2161;
47. e) S. Bhattacharya, S. Sengupta, Tetrahedron Lett. 2004, 45, 8733.
48. Choice of the palladium source and ligands 2 and 4 was made on the basis of our previous reports. See references [3] and [20].
49. a) Use of electron-deficient zinc acetylides allows coupling with aryl halides; see: E.-I. Negishi, L. Anastasia, Chem. Rev. 2003, 103, 1979, and references therein.
50. 3 allows the coupling of electron-deficient terminal alkynes and electron-deficient or neutral aryl iodides; see: T. Eckert, J. Ipaktschi, Synth. Commun. 1998, 28, 327.
51. 3 allows the coupling of electron-deficient terminal alkynes and diphenyliodonium salts; see: U. Radhakrishnan, P. J. Stang, Org. Lett. 2001, 3, 859.
52. d) Water was essential to the coupling reaction of aryl iodides and various alkynoates; see: Y. Uozumi, Y. Kobayashi, Heterocycles 2003, 59, 71.