The first general method for Stille cross-couplings of aryl chlorides

Angewandte Chemie - International Edition

Volumn 38, Issue 16, 1999, Pages 2411-2413

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

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Cross coupling; Homogeneous catalysis; Palladium; Stille reactions

Indexed keywords

PALLADIUM;

ANALYTIC METHOD; ARTICLE; CATALYST; COUPLING FACTOR; DRUG SYNTHESIS; ELECTRON TRANSPORT; LIGAND BINDING; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0033549832     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990816)38:16<2411::AID-ANIE2411>3.0.CO;2-T     Document Type: Article

References (51)

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2. a) J. K. Stille, Angew. Chem. 1986, 98, 504-519; Angew. Chem. Int. Ed. Engl. 1986, 25, 508-524;
3. b) V. Farina, V. Krishnamurthy, W. J. Scott, Org. React. 1997, 50, 1-652;
4. c) T. N. Mitchell in Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), WILEY-VCH, New York, 1998, chap. 4;
5. d) for recent mechanistic work, see: A. L. Casado, P. Espinet, J. Am. Chem. Soc. 1998, 120, 8978-8985.
6. V. V. Grushin, H. Alper, Chem. Rev. 1994, 94, 1047-1062.
7. a) V. Farina, V. Krishnamurthy, W. J. Scott, Org. React. 1997, 50, 12-16;
8. b) reference [1c].
9. 0. For a discussion, see reference [2].
10. 0-catalyzed cross-coupling of aryl halides (including aryl chlorides) with organotin compounds: E. Shirakawa, K. Yamasaki, T. Hiyama, Synthesis 1998, 1544-1549.
11. a) M. Nishiyama, T. Yamamoto, Y. Koie, Tetrahedron Lett. 1998, 39, 617-620 (one example);
12. 0-catalyzed aminations of aryl chlorides, see: N. P. Reddy, M. Tanaka, Tetrahedron Lett. 1997, 38, 4807-4810; B.C. Hamann, J. F. Hartwig, J. Am. Chem. Soc. 1998, 120, 7369-7370; D. W. Old, J. P. Wolfe. S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723.
13. 0-catalyzed aminations of aryl chlorides, see: N. P. Reddy, M. Tanaka, Tetrahedron Lett. 1997, 38, 4807-4810; B.C. Hamann, J. F. Hartwig, J. Am. Chem. Soc. 1998, 120, 7369-7370; D. W. Old, J. P. Wolfe. S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723.
14. 0-catalyzed aminations of aryl chlorides, see: N. P. Reddy, M. Tanaka, Tetrahedron Lett. 1997, 38, 4807-4810; B.C. Hamann, J. F. Hartwig, J. Am. Chem. Soc. 1998, 120, 7369-7370; D. W. Old, J. P. Wolfe. S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723.
15. a) A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388;
16. a) A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388;
17. 0-catalyzed Suzuki reactions of aryl chlorides, see: F. Firooznia, C. Gude, K. Chan, Y. Satoh, Tetrahedron Lett. 1998, 39, 3985-3988; D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723.
18. 0-catalyzed Suzuki reactions of aryl chlorides, see: F. Firooznia, C. Gude, K. Chan, Y. Satoh, Tetrahedron Lett. 1998, 39, 3985-3988; D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723.
19. M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 1473-1478.
20. 0-catalyzed Heck reactions of aryl chlorides, see: Y. Ben-David, M. Portnoy, M. Gozin, D. Milstein, Organometallics 1992, 11, 1995-1996; M. Portnoy, Y. Ben-David, D. Milstein, Organometallics 1993, 12, 4734-4735.
21. 0-catalyzed Heck reactions of aryl chlorides, see: Y. Ben-David, M. Portnoy, M. Gozin, D. Milstein, Organometallics 1992, 11, 1995-1996; M. Portnoy, Y. Ben-David, D. Milstein, Organometallics 1993, 12, 4734-4735.
22. 0-catalyzed Heck reactions of aryl chlorides, see: Y. Ben-David, M. Portnoy, M. Gozin, D. Milstein, Organometallics 1992, 11, 1995-1996; M. Portnoy, Y. Ben-David, D. Milstein, Organometallics 1993, 12, 4734-4735.
23. 0-catalyzed Heck reactions of aryl chlorides, see: Y. Ben-David, M. Portnoy, M. Gozin, D. Milstein, Organometallics 1992, 11, 1995-1996; M. Portnoy, Y. Ben-David, D. Milstein, Organometallics 1993, 12, 4734-4735.
24. Chemistry of Tin (Ed.: P. J. Smith), Blackie, New York, 1998.
25. a) For example, tetrabutylammonium difluorotriphenylstannate has been reported to be an effective phenylating agent in Stille reactions of aryl triflates: A. G. Martinez, J. O. Barcina, A. de F. Cerezo, L. R. Subramanian, Synlett 1994, 1047-1048;
26. b) E. Fouquet, M. Pereyre, A. L. Rodriguez, J. Org. Chem. 1997, 62, 5242-5243; E. Fouquet, A. L. Rodriguez, Synlett 1998, 1323-1324.
27. b) E. Fouquet, M. Pereyre, A. L. Rodriguez, J. Org. Chem. 1997, 62, 5242-5243; E. Fouquet, A. L. Rodriguez, Synlett 1998, 1323-1324.
28. For examples of enhanced reactivity in Stille reactions due to intramolecular coordination of a nucleophile to an organotin reagent, see: a) E. Vedejs, A. R. Haight, W. O. Moss, J. Am. Chem. Soc. 1992, 114, 6556-6558; b) J. M. Brown, M. Pearson, J. T. B. H. Jastrzebski, G. van Koten, J. Chem. Soc. Chem. Commun. 1992, 1440-1441; c) V. Farina, Pure Appl. Chem. 1996, 68, 73-78; d) E. Fouquet, M. Pereyre, A. L. Rodriguez, J. Org. Chem. 1997, 62, 5242-5243.
29. For examples of enhanced reactivity in Stille reactions due to intramolecular coordination of a nucleophile to an organotin reagent, see: a) E. Vedejs, A. R. Haight, W. O. Moss, J. Am. Chem. Soc. 1992, 114, 6556-6558; b) J. M. Brown, M. Pearson, J. T. B. H. Jastrzebski, G. van Koten, J. Chem. Soc. Chem. Commun. 1992, 1440-1441; c) V. Farina, Pure Appl. Chem. 1996, 68, 73-78; d) E. Fouquet, M. Pereyre, A. L. Rodriguez, J. Org. Chem. 1997, 62, 5242-5243.
30. For examples of enhanced reactivity in Stille reactions due to intramolecular coordination of a nucleophile to an organotin reagent, see: a) E. Vedejs, A. R. Haight, W. O. Moss, J. Am. Chem. Soc. 1992, 114, 6556-6558; b) J. M. Brown, M. Pearson, J. T. B. H. Jastrzebski, G. van Koten, J. Chem. Soc. Chem. Commun. 1992, 1440-1441; c) V. Farina, Pure Appl. Chem. 1996, 68, 73-78; d) E. Fouquet, M. Pereyre, A. L. Rodriguez, J. Org. Chem. 1997, 62, 5242-5243.
31. For examples of enhanced reactivity in Stille reactions due to intramolecular coordination of a nucleophile to an organotin reagent, see: a) E. Vedejs, A. R. Haight, W. O. Moss, J. Am. Chem. Soc. 1992, 114, 6556-6558; b) J. M. Brown, M. Pearson, J. T. B. H. Jastrzebski, G. van Koten, J. Chem. Soc. Chem. Commun. 1992, 1440-1441; c) V. Farina, Pure Appl. Chem. 1996, 68, 73-78; d) E. Fouquet, M. Pereyre, A. L. Rodriguez, J. Org. Chem. 1997, 62, 5242-5243.
32. a) Electron-poor aryl chlorides with organosilicon compounds: K.-i. Gouda, E. Hagiwara, Y. Hatanaka, T. Hiyama, J. Org. Chem. 1996, 61, 7232-7233;
33. b) aryl halides (bromides, iodides) with organosilicon compounds: T. Hiyama in Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), WILEY-VCH, New York, 1998. chap. 10;
34. c) aryl bromides and triflates with organoboron compounds: S. W. Wright, D. L. Hageman, L. D. McClure, J. Org. Chem. 1994, 59, 6095-6097.
35. K. Fugami, S.-y. Ohnuma, M. Kameyama, T. Saotome, M. Kosugi, Synlett 1999, 63-64.
36. For Stille cross-couplings of aryl bromides and aryl iodides in the presence of hydroxide, see: A. I. Roshchin, N. A. Bumagin, I. P. Beletskaya, Tetrahedron Lett. 1995, 36, 125-128.
37. For Hiyama cross-couplings in the presence of hydroxide, see: E. Hagiwara, K.-i. Gouda, Y. Hatanaka, T. Hiyama, Tetrahedron Lett. 1997, 38, 439-442. See also: C. Mateo, C Fernandez-Rivas, D. J. Cardenas, A. M. Echavarren, Organometallics 1998, 17, 3661-3669.
38. For Hiyama cross-couplings in the presence of hydroxide, see: E. Hagiwara, K.-i. Gouda, Y. Hatanaka, T. Hiyama, Tetrahedron Lett. 1997, 38, 439-442. See also: C. Mateo, C Fernandez-Rivas, D. J. Cardenas, A. M. Echavarren, Organometallics 1998, 17, 3661-3669.
39. The reaction with NaOH as the additive was somewhat less clean than the reaction with CsF.
40. 2O washings were concentrated by rotary evaporation. The product was then purified by flash chromatography.
41. 3 affords 4-n-butylstyrene in 67% yield.
42. Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), WILEY-VCH, New York, 1998.
43. In the Stille cross-couplings of the other organostannanes illustrated in Table 3, essentially no butyl transfer is observed (< 2%).
44. For a general discussion of the problem of separating reaction products from organotin residues, see: D. Crich, S. Sun, J. Org. Chem. 1996, 61, 7200-7201.
45. M. Hoshino, P. Degenkolb, D. P. Curran, J. Org. Chem. 1997, 62, 8341-8349; D. P. Curran, Angew. Chem. 1998, 110, 1230-1255; Angew. Chem. Int. Ed. 1998, 37, 1174-1196.
46. M. Hoshino, P. Degenkolb, D. P. Curran, J. Org. Chem. 1997, 62, 8341-8349; D. P. Curran, Angew. Chem. 1998, 110, 1230-1255; Angew. Chem. Int. Ed. 1998, 37, 1174-1196.
47. M. Hoshino, P. Degenkolb, D. P. Curran, J. Org. Chem. 1997, 62, 8341-8349; D. P. Curran, Angew. Chem. 1998, 110, 1230-1255; Angew. Chem. Int. Ed. 1998, 37, 1174-1196.
48. a) Addition of fluoride (e.g., KF) after a reaction is complete is a common method for removing organotin halide impurities: D. Milstein, J. K. Stille, J. Am. Chem. Soc. 1978, 100, 3636-3638; J. E. Liebner, J. Jacobus, J. Org. Chem. 1979, 44, 449-450.
49. a) Addition of fluoride (e.g., KF) after a reaction is complete is a common method for removing organotin halide impurities: D. Milstein, J. K. Stille, J. Am. Chem. Soc. 1978, 100, 3636-3638; J. E. Liebner, J. Jacobus, J. Org. Chem. 1979, 44, 449-450.
50. b) Stille and Scott have reported that the addition of CsF to cross-coupling reactions of vinyl Inflates with organotin compounds leads to ∼80% removal of tin: W. J. Scott, J. K. Stille, J. Am. Chem. Soc. 1986, 108, 3033-3040.
51. 3SnCl at the end of the reaction.