Synthesis of unsymmetrical biaryls by palladium-catalyzed cross coupling reactions of arenes with tetrabutylammonium triphenyldifluorosilicate, a hypervalent silicon reagent

Journal of Organic Chemistry

Volumn 64, Issue 9, 1999, Pages 3266-3270

  Mowery, Molly E ^a   DeShong, Philip ^a  

^a Bldg 142   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMIDE; IODIDE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SILICON DERIVATIVE; TETRABUTYLAMMONIUM TRIPHENYLDIFLUOROSILICATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 0033617214     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990072c     Document Type: Article

References (62)

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5. For information about recent advances in elucidating the mechanism of the Stille reaction, see: (a) Casado, A. L.; Espinet, P. J. Am. Chem. Soc. 1998, 120, 8978-8985. (b) Casado, A. L.; Espinet, P. Organometallics 1998, 17, 954-959. For information concerning the mechanism of the related Heck reaction, see: (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427-436. For other articles about the Stille reaction, see: (d) Stille, J. K.; Echavarren, A. M.; Williams, R. M.; Hendrix, J. A. Org. Synth. 1992, 71, 97-106 and references therein. (e) Del Valle, L.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1990, 55, 3019-3023. (f) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478-5486. (g) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813-817. (h) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524. (i) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3-3040. (j) Stille, J. K. Pure Appl. Chem. 1985, 57, 1771-1780. (k) Farina, V.; Krishnaumurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (l) Farina, V. Pure Appl. Chem. 1996, 68, 73-78. (m) Farina, V.; Roth, G. P. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; J. A. I.: Greenwich, 1995; Vol. 5.
6. For information about recent advances in elucidating the mechanism of the Stille reaction, see: (a) Casado, A. L.; Espinet, P. J. Am. Chem. Soc. 1998, 120, 8978-8985. (b) Casado, A. L.; Espinet, P. Organometallics 1998, 17, 954-959. For information concerning the mechanism of the related Heck reaction, see: (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427-436. For other articles about the Stille reaction, see: (d) Stille, J. K.; Echavarren, A. M.; Williams, R. M.; Hendrix, J. A. Org. Synth. 1992, 71, 97-106 and references therein. (e) Del Valle, L.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1990, 55, 3019-3023. (f) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478-5486. (g) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813-817. (h) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524. (i) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3-3040. (j) Stille, J. K. Pure Appl. Chem. 1985, 57, 1771-1780. (k) Farina, V.; Krishnaumurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (l) Farina, V. Pure Appl. Chem. 1996, 68, 73-78. (m) Farina, V.; Roth, G. P. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; J. A. I.: Greenwich, 1995; Vol. 5.
7. For information about recent advances in elucidating the mechanism of the Stille reaction, see: (a) Casado, A. L.; Espinet, P. J. Am. Chem. Soc. 1998, 120, 8978-8985. (b) Casado, A. L.; Espinet, P. Organometallics 1998, 17, 954-959. For information concerning the mechanism of the related Heck reaction, see: (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427-436. For other articles about the Stille reaction, see: (d) Stille, J. K.; Echavarren, A. M.; Williams, R. M.; Hendrix, J. A. Org. Synth. 1992, 71, 97-106 and references therein. (e) Del Valle, L.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1990, 55, 3019-3023. (f) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478-5486. (g) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813-817. (h) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524. (i) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3-3040. (j) Stille, J. K. Pure Appl. Chem. 1985, 57, 1771-1780. (k) Farina, V.; Krishnaumurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (l) Farina, V. Pure Appl. Chem. 1996, 68, 73-78. (m) Farina, V.; Roth, G. P. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; J. A. I.: Greenwich, 1995; Vol. 5.
8. For information about recent advances in elucidating the mechanism of the Stille reaction, see: (a) Casado, A. L.; Espinet, P. J. Am. Chem. Soc. 1998, 120, 8978-8985. (b) Casado, A. L.; Espinet, P. Organometallics 1998, 17, 954-959. For information concerning the mechanism of the related Heck reaction, see: (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427-436. For other articles about the Stille reaction, see: (d) Stille, J. K.; Echavarren, A. M.; Williams, R. M.; Hendrix, J. A. Org. Synth. 1992, 71, 97-106 and references therein. (e) Del Valle, L.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1990, 55, 3019-3023. (f) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478-5486. (g) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813-817. (h) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524. (i) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3-3040. (j) Stille, J. K. Pure Appl. Chem. 1985, 57, 1771-1780. (k) Farina, V.; Krishnaumurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (l) Farina, V. Pure Appl. Chem. 1996, 68, 73-78. (m) Farina, V.; Roth, G. P. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; J. A. I.: Greenwich, 1995; Vol. 5.
9. For information about recent advances in elucidating the mechanism of the Stille reaction, see: (a) Casado, A. L.; Espinet, P. J. Am. Chem. Soc. 1998, 120, 8978-8985. (b) Casado, A. L.; Espinet, P. Organometallics 1998, 17, 954-959. For information concerning the mechanism of the related Heck reaction, see: (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427-436. For other articles about the Stille reaction, see: (d) Stille, J. K.; Echavarren, A. M.; Williams, R. M.; Hendrix, J. A. Org. Synth. 1992, 71, 97-106 and references therein. (e) Del Valle, L.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1990, 55, 3019-3023. (f) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478-5486. (g) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813-817. (h) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524. (i) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3-3040. (j) Stille, J. K. Pure Appl. Chem. 1985, 57, 1771-1780. (k) Farina, V.; Krishnaumurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (l) Farina, V. Pure Appl. Chem. 1996, 68, 73-78. (m) Farina, V.; Roth, G. P. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; J. A. I.: Greenwich, 1995; Vol. 5.
10. For information about recent advances in elucidating the mechanism of the Stille reaction, see: (a) Casado, A. L.; Espinet, P. J. Am. Chem. Soc. 1998, 120, 8978-8985. (b) Casado, A. L.; Espinet, P. Organometallics 1998, 17, 954-959. For information concerning the mechanism of the related Heck reaction, see: (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427-436. For other articles about the Stille reaction, see: (d) Stille, J. K.; Echavarren, A. M.; Williams, R. M.; Hendrix, J. A. Org. Synth. 1992, 71, 97-106 and references therein. (e) Del Valle, L.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1990, 55, 3019-3023. (f) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478-5486. (g) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813-817. (h) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524. (i) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3-3040. (j) Stille, J. K. Pure Appl. Chem. 1985, 57, 1771-1780. (k) Farina, V.; Krishnaumurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (l) Farina, V. Pure Appl. Chem. 1996, 68, 73-78. (m) Farina, V.; Roth, G. P. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; J. A. I.: Greenwich, 1995; Vol. 5.
11. For information about recent advances in elucidating the mechanism of the Stille reaction, see: (a) Casado, A. L.; Espinet, P. J. Am. Chem. Soc. 1998, 120, 8978-8985. (b) Casado, A. L.; Espinet, P. Organometallics 1998, 17, 954-959. For information concerning the mechanism of the related Heck reaction, see: (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427-436. For other articles about the Stille reaction, see: (d) Stille, J. K.; Echavarren, A. M.; Williams, R. M.; Hendrix, J. A. Org. Synth. 1992, 71, 97-106 and references therein. (e) Del Valle, L.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1990, 55, 3019-3023. (f) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478-5486. (g) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813-817. (h) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524. (i) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3-3040. (j) Stille, J. K. Pure Appl. Chem. 1985, 57, 1771-1780. (k) Farina, V.; Krishnaumurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (l) Farina, V. Pure Appl. Chem. 1996, 68, 73-78. (m) Farina, V.; Roth, G. P. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; J. A. I.: Greenwich, 1995; Vol. 5.
12. For information about recent advances in elucidating the mechanism of the Stille reaction, see: (a) Casado, A. L.; Espinet, P. J. Am. Chem. Soc. 1998, 120, 8978-8985. (b) Casado, A. L.; Espinet, P. Organometallics 1998, 17, 954-959. For information concerning the mechanism of the related Heck reaction, see: (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427-436. For other articles about the Stille reaction, see: (d) Stille, J. K.; Echavarren, A. M.; Williams, R. M.; Hendrix, J. A. Org. Synth. 1992, 71, 97-106 and references therein. (e) Del Valle, L.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1990, 55, 3019-3023. (f) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478-5486. (g) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813-817. (h) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524. (i) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3-3040. (j) Stille, J. K. Pure Appl. Chem. 1985, 57, 1771-1780. (k) Farina, V.; Krishnaumurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (l) Farina, V. Pure Appl. Chem. 1996, 68, 73-78. (m) Farina, V.; Roth, G. P. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; J. A. I.: Greenwich, 1995; Vol. 5.
13. For information about recent advances in elucidating the mechanism of the Stille reaction, see: (a) Casado, A. L.; Espinet, P. J. Am. Chem. Soc. 1998, 120, 8978-8985. (b) Casado, A. L.; Espinet, P. Organometallics 1998, 17, 954-959. For information concerning the mechanism of the related Heck reaction, see: (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427-436. For other articles about the Stille reaction, see: (d) Stille, J. K.; Echavarren, A. M.; Williams, R. M.; Hendrix, J. A. Org. Synth. 1992, 71, 97-106 and references therein. (e) Del Valle, L.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1990, 55, 3019-3023. (f) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478-5486. (g) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813-817. (h) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524. (i) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3-3040. (j) Stille, J. K. Pure Appl. Chem. 1985, 57, 1771-1780. (k) Farina, V.; Krishnaumurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (l) Farina, V. Pure Appl. Chem. 1996, 68, 73-78. (m) Farina, V.; Roth, G. P. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; J. A. I.: Greenwich, 1995; Vol. 5.
14. For information about recent advances in elucidating the mechanism of the Stille reaction, see: (a) Casado, A. L.; Espinet, P. J. Am. Chem. Soc. 1998, 120, 8978-8985. (b) Casado, A. L.; Espinet, P. Organometallics 1998, 17, 954-959. For information concerning the mechanism of the related Heck reaction, see: (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427-436. For other articles about the Stille reaction, see: (d) Stille, J. K.; Echavarren, A. M.; Williams, R. M.; Hendrix, J. A. Org. Synth. 1992, 71, 97-106 and references therein. (e) Del Valle, L.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1990, 55, 3019-3023. (f) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478-5486. (g) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813-817. (h) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524. (i) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3-3040. (j) Stille, J. K. Pure Appl. Chem. 1985, 57, 1771-1780. (k) Farina, V.; Krishnaumurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (l) Farina, V. Pure Appl. Chem. 1996, 68, 73-78. (m) Farina, V.; Roth, G. P. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; J. A. I.: Greenwich, 1995; Vol. 5.
15. For information about recent advances in elucidating the mechanism of the Stille reaction, see: (a) Casado, A. L.; Espinet, P. J. Am. Chem. Soc. 1998, 120, 8978-8985. (b) Casado, A. L.; Espinet, P. Organometallics 1998, 17, 954-959. For information concerning the mechanism of the related Heck reaction, see: (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427-436. For other articles about the Stille reaction, see: (d) Stille, J. K.; Echavarren, A. M.; Williams, R. M.; Hendrix, J. A. Org. Synth. 1992, 71, 97-106 and references therein. (e) Del Valle, L.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1990, 55, 3019-3023. (f) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478-5486. (g) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813-817. (h) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524. (i) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3-3040. (j) Stille, J. K. Pure Appl. Chem. 1985, 57, 1771-1780. (k) Farina, V.; Krishnaumurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (l) Farina, V. Pure Appl. Chem. 1996, 68, 73-78. (m) Farina, V.; Roth, G. P. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; J. A. I.: Greenwich, 1995; Vol. 5.
16. For information about recent advances in elucidating the mechanism of the Stille reaction, see: (a) Casado, A. L.; Espinet, P. J. Am. Chem. Soc. 1998, 120, 8978-8985. (b) Casado, A. L.; Espinet, P. Organometallics 1998, 17, 954-959. For information concerning the mechanism of the related Heck reaction, see: (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427-436. For other articles about the Stille reaction, see: (d) Stille, J. K.; Echavarren, A. M.; Williams, R. M.; Hendrix, J. A. Org. Synth. 1992, 71, 97-106 and references therein. (e) Del Valle, L.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1990, 55, 3019-3023. (f) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478-5486. (g) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813-817. (h) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524. (i) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3-3040. (j) Stille, J. K. Pure Appl. Chem. 1985, 57, 1771-1780. (k) Farina, V.; Krishnaumurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (l) Farina, V. Pure Appl. Chem. 1996, 68, 73-78. (m) Farina, V.; Roth, G. P. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; J. A. I.: Greenwich, 1995; Vol. 5.
17. For information about recent advances in elucidating the mechanism of the Stille reaction, see: (a) Casado, A. L.; Espinet, P. J. Am. Chem. Soc. 1998, 120, 8978-8985. (b) Casado, A. L.; Espinet, P. Organometallics 1998, 17, 954-959. For information concerning the mechanism of the related Heck reaction, see: (c) Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427-436. For other articles about the Stille reaction, see: (d) Stille, J. K.; Echavarren, A. M.; Williams, R. M.; Hendrix, J. A. Org. Synth. 1992, 71, 97-106 and references therein. (e) Del Valle, L.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1990, 55, 3019-3023. (f) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478-5486. (g) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813-817. (h) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524. (i) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3-3040. (j) Stille, J. K. Pure Appl. Chem. 1985, 57, 1771-1780. (k) Farina, V.; Krishnaumurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (l) Farina, V. Pure Appl. Chem. 1996, 68, 73-78. (m) Farina, V.; Roth, G. P. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; J. A. I.: Greenwich, 1995; Vol. 5.
18. For examples of natural product syntheses using Stille coupling, see: (a) Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883-2894; and references therein. (b) Gyorkos, A. C.; Stille, J. K.; Hegedus, L. S. J. Am. Chem. Soc. 1990, 112, 8465-8472. (c) Discodermolide: Smith, A. B., III.; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011-12012. (d) Rapamycin: Nicolaou, K. C.; Chakraborty, T. K.; Piscopio, A. D.; Minowa, N.; Bertinato, P. J. Am. Chem. Soc. 1993, 115, 4419-4420.
19. For examples of natural product syntheses using Stille coupling, see: (a) Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883-2894; and references therein. (b) Gyorkos, A. C.; Stille, J. K.; Hegedus, L. S. J. Am. Chem. Soc. 1990, 112, 8465-8472. (c) Discodermolide: Smith, A. B., III.; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011-12012. (d) Rapamycin: Nicolaou, K. C.; Chakraborty, T. K.; Piscopio, A. D.; Minowa, N.; Bertinato, P. J. Am. Chem. Soc. 1993, 115, 4419-4420.
20. For examples of natural product syntheses using Stille coupling, see: (a) Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883-2894; and references therein. (b) Gyorkos, A. C.; Stille, J. K.; Hegedus, L. S. J. Am. Chem. Soc. 1990, 112, 8465-8472. (c) Discodermolide: Smith, A. B., III.; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011-12012. (d) Rapamycin: Nicolaou, K. C.; Chakraborty, T. K.; Piscopio, A. D.; Minowa, N.; Bertinato, P. J. Am. Chem. Soc. 1993, 115, 4419-4420.
21. For examples of natural product syntheses using Stille coupling, see: (a) Kalivretenos, A.; Stille, J. K.; Hegedus, L. S. J. Org. Chem. 1991, 56, 2883-2894; and references therein. (b) Gyorkos, A. C.; Stille, J. K.; Hegedus, L. S. J. Am. Chem. Soc. 1990, 112, 8465-8472. (c) Discodermolide: Smith, A. B., III.; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011-12012. (d) Rapamycin: Nicolaou, K. C.; Chakraborty, T. K.; Piscopio, A. D.; Minowa, N.; Bertinato, P. J. Am. Chem. Soc. 1993, 115, 4419-4420.
22. For information regarding toxicology studies of tin reagents, see: (a) Arakawa, Y. In Chemistry of Tin, 2nd ed.; Smith, P. J., Ed.; Blackie Academic & Professional: London, 1998; pp 388-428. (b) Smith, P. J., ref 4a, pp 429-441. (c) Aldridge, W. N. In Chemistry and Technology of Silicon and Tin; Kumar Das, V. G., Weng, N. G., Gielen, M., Eds.; Oxford University Press: New York, 1992; pp 78-92.
23. For information regarding toxicology studies of tin reagents, see: (a) Arakawa, Y. In Chemistry of Tin, 2nd ed.; Smith, P. J., Ed.; Blackie Academic & Professional: London, 1998; pp 388-428. (b) Smith, P. J., ref 4a, pp 429-441. (c) Aldridge, W. N. In Chemistry and Technology of Silicon and Tin; Kumar Das, V. G., Weng, N. G., Gielen, M., Eds.; Oxford University Press: New York, 1992; pp 78-92.
24. For information regarding toxicology studies of tin reagents, see: (a) Arakawa, Y. In Chemistry of Tin, 2nd ed.; Smith, P. J., Ed.; Blackie Academic & Professional: London, 1998; pp 388-428. (b) Smith, P. J., ref 4a, pp 429-441. (c) Aldridge, W. N. In Chemistry and Technology of Silicon and Tin; Kumar Das, V. G., Weng, N. G., Gielen, M., Eds.; Oxford University Press: New York, 1992; pp 78-92.
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32. For recent reviews on organosilicon compounds and cross coupling reactions, see: (a) Hiyama, T. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinhein, Germany, 1998; pp 421-452. (b) Horn, K. A. Chem. Rev. 1995, 95, 1317-1350. (c) Hiyama, T.; Hatanaka, Y. Pure Appl. Chem. 1994, 66, 1417-1478. (d) Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1317-1448.
33. For recent reviews on organosilicon compounds and cross coupling reactions, see: (a) Hiyama, T. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinhein, Germany, 1998; pp 421-452. (b) Horn, K. A. Chem. Rev. 1995, 95, 1317-1350. (c) Hiyama, T.; Hatanaka, Y. Pure Appl. Chem. 1994, 66, 1417-1478. (d) Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1317-1448.
34. For recent reviews on organosilicon compounds and cross coupling reactions, see: (a) Hiyama, T. In Metal-catalyzed Cross- coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinhein, Germany, 1998; pp 421-452. (b) Horn, K. A. Chem. Rev. 1995, 95, 1317-1350. (c) Hiyama, T.; Hatanaka, Y. Pure Appl. Chem. 1994, 66, 1417-1478. (d) Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1317-1448.
35. For recent reviews on organosilicon compounds and cross coupling reactions, see: (a) Hiyama, T. In Metal-catalyzed Cross- coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinhein, Germany, 1998; pp 421-452. (b) Horn, K. A. Chem. Rev. 1995, 95, 1317-1350. (c) Hiyama, T.; Hatanaka, Y. Pure Appl. Chem. 1994, 66, 1417-1478. (d) Chuit, C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1317-1448.
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37. For information about Pd-catalyzed, fluoride-promoted cross coupling reactions of reactions of organohalosilanes with aryl and alkenyl halides, see: (a) Gouda, K.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1996, 61, 7232-7233. (b) Hatanaka, Y.; Goda, K.; Okahara, Y.; Hiyama, T. Tetrahedron 1994, 50, 8301-8316. (c) Hatanaka, Y.; Fukushima, S.; Hiyama, T. Heterocycles 1990, 30, 303-306. (d) Hatanaka, Y.; Fukushima, S.; Hiyama, T. Chem. Lett. 1989, 1711-1714. For information about alkylation of aryl halides with alkyltrifluorosilanes, see: (e) Matsuhashi, H.; Asai, S.; Hirabayashi, K.; Hatanaka, Y.; Mori, A. Hiyama, T. Bull. Chem. Soc. Jpn. 1997, 70, 437-444. (f) Matsuhashi, H.; Kuroboshi, M.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1994, 35, 6507-6510. For information about Pd- catalyzed, NaOH-promoted reactions of organochlorosilanes with aryl chlorides, see: (g) Hagiwara, E.; Gouda, K.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1997, 38, 439-442.
38. For information about Pd-catalyzed, fluoride-promoted cross coupling reactions of reactions of organohalosilanes with aryl and alkenyl halides, see: (a) Gouda, K.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1996, 61, 7232-7233. (b) Hatanaka, Y.; Goda, K.; Okahara, Y.; Hiyama, T. Tetrahedron 1994, 50, 8301-8316. (c) Hatanaka, Y.; Fukushima, S.; Hiyama, T. Heterocycles 1990, 30, 303-306. (d) Hatanaka, Y.; Fukushima, S.; Hiyama, T. Chem. Lett. 1989, 1711-1714. For information about alkylation of aryl halides with alkyltrifluorosilanes, see: (e) Matsuhashi, H.; Asai, S.; Hirabayashi, K.; Hatanaka, Y.; Mori, A. Hiyama, T. Bull. Chem. Soc. Jpn. 1997, 70, 437-444. (f) Matsuhashi, H.; Kuroboshi, M.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1994, 35, 6507-6510. For information about Pd- catalyzed, NaOH-promoted reactions of organochlorosilanes with aryl chlorides, see: (g) Hagiwara, E.; Gouda, K.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1997, 38, 439-442.
39. For information about Pd-catalyzed, fluoride-promoted cross coupling reactions of reactions of organohalosilanes with aryl and alkenyl halides, see: (a) Gouda, K.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1996, 61, 7232-7233. (b) Hatanaka, Y.; Goda, K.; Okahara, Y.; Hiyama, T. Tetrahedron 1994, 50, 8301-8316. (c) Hatanaka, Y.; Fukushima, S.; Hiyama, T. Heterocycles 1990, 30, 303-306. (d) Hatanaka, Y.; Fukushima, S.; Hiyama, T. Chem. Lett. 1989, 1711-1714. For information about alkylation of aryl halides with alkyltrifluorosilanes, see: (e) Matsuhashi, H.; Asai, S.; Hirabayashi, K.; Hatanaka, Y.; Mori, A. Hiyama, T. Bull. Chem. Soc. Jpn. 1997, 70, 437-444. (f) Matsuhashi, H.; Kuroboshi, M.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1994, 35, 6507-6510. For information about Pd- catalyzed, NaOH-promoted reactions of organochlorosilanes with aryl chlorides, see: (g) Hagiwara, E.; Gouda, K.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1997, 38, 439-442.
40. For information about Pd-catalyzed, fluoride-promoted cross coupling reactions of reactions of organohalosilanes with aryl and alkenyl halides, see: (a) Gouda, K.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1996, 61, 7232-7233. (b) Hatanaka, Y.; Goda, K.; Okahara, Y.; Hiyama, T. Tetrahedron 1994, 50, 8301-8316. (c) Hatanaka, Y.; Fukushima, S.; Hiyama, T. Heterocycles 1990, 30, 303-306. (d) Hatanaka, Y.; Fukushima, S.; Hiyama, T. Chem. Lett. 1989, 1711-1714. For information about alkylation of aryl halides with alkyltrifluorosilanes, see: (e) Matsuhashi, H.; Asai, S.; Hirabayashi, K.; Hatanaka, Y.; Mori, A. Hiyama, T. Bull. Chem. Soc. Jpn. 1997, 70, 437-444. (f) Matsuhashi, H.; Kuroboshi, M.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1994, 35, 6507-6510. For information about Pd- catalyzed, NaOH-promoted reactions of organochlorosilanes with aryl chlorides, see: (g) Hagiwara, E.; Gouda, K.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1997, 38, 439-442.
41. For information about Pd-catalyzed, fluoride-promoted cross coupling reactions of reactions of organohalosilanes with aryl and alkenyl halides, see: (a) Gouda, K.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1996, 61, 7232-7233. (b) Hatanaka, Y.; Goda, K.; Okahara, Y.; Hiyama, T. Tetrahedron 1994, 50, 8301-8316. (c) Hatanaka, Y.; Fukushima, S.; Hiyama, T. Heterocycles 1990, 30, 303-306. (d) Hatanaka, Y.; Fukushima, S.; Hiyama, T. Chem. Lett. 1989, 1711-1714. For information about alkylation of aryl halides with alkyltrifluorosilanes, see: (e) Matsuhashi, H.; Asai, S.; Hirabayashi, K.; Hatanaka, Y.; Mori, A. Hiyama, T. Bull. Chem. Soc. Jpn. 1997, 70, 437-444. (f) Matsuhashi, H.; Kuroboshi, M.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1994, 35, 6507-6510. For information about Pd- catalyzed, NaOH-promoted reactions of organochlorosilanes with aryl chlorides, see: (g) Hagiwara, E.; Gouda, K.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1997, 38, 439-442.
42. For information about Pd-catalyzed, fluoride-promoted cross coupling reactions of reactions of organohalosilanes with aryl and alkenyl halides, see: (a) Gouda, K.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1996, 61, 7232-7233. (b) Hatanaka, Y.; Goda, K.; Okahara, Y.; Hiyama, T. Tetrahedron 1994, 50, 8301-8316. (c) Hatanaka, Y.; Fukushima, S.; Hiyama, T. Heterocycles 1990, 30, 303-306. (d) Hatanaka, Y.; Fukushima, S.; Hiyama, T. Chem. Lett. 1989, 1711-1714. For information about alkylation of aryl halides with alkyltrifluorosilanes, see: (e) Matsuhashi, H.; Asai, S.; Hirabayashi, K.; Hatanaka, Y.; Mori, A. Hiyama, T. Bull. Chem. Soc. Jpn. 1997, 70, 437-444. (f) Matsuhashi, H.; Kuroboshi, M.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1994, 35, 6507-6510. For information about Pd- catalyzed, NaOH-promoted reactions of organochlorosilanes with aryl chlorides, see: (g) Hagiwara, E.; Gouda, K.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1997, 38, 439-442.
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