A New Synthesis of Butadienyl- and Styrylboronic Esters: Highly Reactive Intermediates for Suzuki Cross-Coupling

Organic Letters

Volumn 4, Issue 8, 2002, Pages 1275-1277

  Tivola, Paolo Balma ^a   Deagostino, Annamaria ^a   Prandi, Cristina ^b   Venturello, Paolo ^a  

^a UNIVERSITY OF TURIN   (Italy)

^b Dipartimento Di Scienze E Tecnologie Avanzate   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0442267289     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0255817     Document Type: Article

References (42)

1. For reviews, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. Stanforth, S. P. Tetrahedron 1998, 54, 263-303. Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168.
2. For reviews, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. Stanforth, S. P. Tetrahedron 1998, 54, 263-303. Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168.
3. For reviews, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. Stanforth, S. P. Tetrahedron 1998, 54, 263-303. Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168.
4. Stille, J. K.; Milstein, D. J. Am. Chem. Soc. 1978, 100, 3636-3638. For reviews, see: Stille, J. K. Angew. Chem., Int. Ed Engl. 1986, 25, 508-524. Farina, V. Pure Appl. Chem. 1996, 68, 73-78. Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652.
5. Stille, J. K.; Milstein, D. J. Am. Chem. Soc. 1978, 100, 3636-3638. For reviews, see: Stille, J. K. Angew. Chem., Int. Ed Engl. 1986, 25, 508-524. Farina, V. Pure Appl. Chem. 1996, 68, 73-78. Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652.
6. Stille, J. K.; Milstein, D. J. Am. Chem. Soc. 1978, 100, 3636-3638. For reviews, see: Stille, J. K. Angew. Chem., Int. Ed Engl. 1986, 25, 508-524. Farina, V. Pure Appl. Chem. 1996, 68, 73-78. Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652.
7. Stille, J. K.; Milstein, D. J. Am. Chem. Soc. 1978, 100, 3636-3638. For reviews, see: Stille, J. K. Angew. Chem., Int. Ed Engl. 1986, 25, 508-524. Farina, V. Pure Appl. Chem. 1996, 68, 73-78. Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652.
8. Boyer, J. Toxicology 1989, 55, 253-298.
9. Littke, F.; Fu, G. C. Angew. Chem., Int. Ed. Engl. 1998, 37, 3387-3388. Wolfe, J. P.; Buchwald, L. Angew. Chem., Int. Ed. 1999, 38, 2413-2414. Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804-3805. Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020-4028. LeBlond, C. R.; Andrews, A. T.; Sun, Y.; Sowa, J. R., Jr. Org. Lett. 2001, 3, 1555-1557.
10. Littke, F.; Fu, G. C. Angew. Chem., Int. Ed. Engl. 1998, 37, 3387-3388. Wolfe, J. P.; Buchwald, L. Angew. Chem., Int. Ed. 1999, 38, 2413-2414. Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804-3805. Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020-4028. LeBlond, C. R.; Andrews, A. T.; Sun, Y.; Sowa, J. R., Jr. Org. Lett. 2001, 3, 1555-1557.
11. Littke, F.; Fu, G. C. Angew. Chem., Int. Ed. Engl. 1998, 37, 3387-3388. Wolfe, J. P.; Buchwald, L. Angew. Chem., Int. Ed. 1999, 38, 2413-2414. Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804-3805. Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020-4028. LeBlond, C. R.; Andrews, A. T.; Sun, Y.; Sowa, J. R., Jr. Org. Lett. 2001, 3, 1555-1557.
12. Littke, F.; Fu, G. C. Angew. Chem., Int. Ed. Engl. 1998, 37, 3387-3388. Wolfe, J. P.; Buchwald, L. Angew. Chem., Int. Ed. 1999, 38, 2413-2414. Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804-3805. Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020-4028. LeBlond, C. R.; Andrews, A. T.; Sun, Y.; Sowa, J. R., Jr. Org. Lett. 2001, 3, 1555-1557.
13. Littke, F.; Fu, G. C. Angew. Chem., Int. Ed. Engl. 1998, 37, 3387-3388. Wolfe, J. P.; Buchwald, L. Angew. Chem., Int. Ed. 1999, 38, 2413-2414. Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804-3805. Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020-4028. LeBlond, C. R.; Andrews, A. T.; Sun, Y.; Sowa, J. R., Jr. Org. Lett. 2001, 3, 1555-1557.
14. Alo, B. I.; Kandil, A.; Patil, P. A.; Sharp, M. J.; Siddiqui, M. A.; Snieckus, V. J. Org. Chem. 1991, 56, 3763-3768. Rocca, P.; Marsais, F.; Godard, A.; Quéguiner, G. Tetrahedron 1993, 49, 49-64.
15. Alo, B. I.; Kandil, A.; Patil, P. A.; Sharp, M. J.; Siddiqui, M. A.; Snieckus, V. J. Org. Chem. 1991, 56, 3763-3768. Rocca, P.; Marsais, F.; Godard, A.; Quéguiner, G. Tetrahedron 1993, 49, 49-64.
16. Kristensen, J.; Lysén, M.; Vedsø, P.; Begtrup, M. Org. Lett. 2001, 3, 1435-1437.
17. Brown, H. C. Organic Syntheses via Boranes; Wiley: New York, 1975. Brown, H. C.; Gupta, S. K. J. Am. Chem. Soc. 1972, 94, 4370-437. Lane, C. F. Tetrahedron 1976, 32, 981-990. Colberg, J. C.; Rane, A.; Soderquist, J. A. J. Am. Chem. Soc. 1993, 115, 6065-6071.
18. Brown, H. C. Organic Syntheses via Boranes; Wiley: New York, 1975. Brown, H. C.; Gupta, S. K. J. Am. Chem. Soc. 1972, 94, 4370-437. Lane, C. F. Tetrahedron 1976, 32, 981-990. Colberg, J. C.; Rane, A.; Soderquist, J. A. J. Am. Chem. Soc. 1993, 115, 6065-6071.
19. Brown, H. C. Organic Syntheses via Boranes; Wiley: New York, 1975. Brown, H. C.; Gupta, S. K. J. Am. Chem. Soc. 1972, 94, 4370-437. Lane, C. F. Tetrahedron 1976, 32, 981-990. Colberg, J. C.; Rane, A.; Soderquist, J. A. J. Am. Chem. Soc. 1993, 115, 6065-6071.
20. Brown, H. C. Organic Syntheses via Boranes; Wiley: New York, 1975. Brown, H. C.; Gupta, S. K. J. Am. Chem. Soc. 1972, 94, 4370-437. Lane, C. F. Tetrahedron 1976, 32, 981-990. Colberg, J. C.; Rane, A.; Soderquist, J. A. J. Am. Chem. Soc. 1993, 115, 6065-6071.
21. Vaultier, M.; Truchet, F.; Carboni, B.; Hoffmann, R. W.; Denne, I. Tetrahedron Lett. 1987, 28, 4169-4172. Renard, P.-Y.; Lallemand, J.-Y. Tetrahedron: Asymmetry 1996, 9, 2523-2424. Six, Y.; Lallemand, J.-Y. Tetrahedron Lett. 1999, 40, 1295-1296 and references therein.
22. Vaultier, M.; Truchet, F.; Carboni, B.; Hoffmann, R. W.; Denne, I. Tetrahedron Lett. 1987, 28, 4169-4172. Renard, P.-Y.; Lallemand, J.-Y. Tetrahedron: Asymmetry 1996, 9, 2523-2424. Six, Y.; Lallemand, J.-Y. Tetrahedron Lett. 1999, 40, 1295-1296 and references therein.
23. Vaultier, M.; Truchet, F.; Carboni, B.; Hoffmann, R. W.; Denne, I. Tetrahedron Lett. 1987, 28, 4169-4172. Renard, P.-Y.; Lallemand, J.-Y. Tetrahedron: Asymmetry 1996, 9, 2523-2424. Six, Y.; Lallemand, J.-Y. Tetrahedron Lett. 1999, 40, 1295-1296 and references therein.
24. Molander, G. A.; Ito, T. Org. Lett. 2001, 3, 393-396.
25. Baker, R.; Bradshaw J. W. S. In Aliphatic and Related Natural Product Chemistry; Gunstone, F. D., Ed.; Specialist Periodical Report, Royal Society of Chemistry: London, 1983; Vol. 3.
26. Nicolau, K. C.; Ramphal, J. Y.; Petasis, N. A.; Serhan, C. N. Angew. Chem., Int. Ed. Engl. 1991, 30, 1100-1116.
27. Launay, V.; Beaudet, I.; Quintard, J.-P. Bull. Soc. Chim. Fr. 1997, 134, 937-946.
28. Dominguez, B.; Iglesia, B.; de Lera, A. R. J. Org. Chem. 1998, 63, 4135-4139.
29. Lipshutz, B. H.; Ullman, B.; Lindsley, C.; Pecchi, S.; Buzard, D. J.; Dickson, D. J. Org. Chem. 1998, 63, 6092-6093.
30. Goldbach, M.; Jäkel, E.; Schneider, M. P. J. Chem. Soc., Chem. Commun. 1987, 1434-1435.
31. Venturello, P. J. Chem. Soc., Chem. Commun. 1992, 1032-1033. Balma Tivola, P.; Deagostino, A.; Prandi, C.; Venturello, P. J. Chem. Soc., Perkin Trans. 1 2001, 437-441 and references therein.
32. Venturello, P. J. Chem. Soc., Chem. Commun. 1992, 1032-1033. Balma Tivola, P.; Deagostino, A.; Prandi, C.; Venturello, P. J. Chem. Soc., Perkin Trans. 1 2001, 437-441 and references therein.
33. Owing to the different mechanism, boronic esters have been obtained with the double bond configuration opposite to that from the hydroboration reaction of alkynes.
34. Wakita, Y.; Yasunaga, T.; Akita, M.; Kojima, M. J. Organomet. Chem. 1986, 301, C17-C20. Grigg, R.; Redpath, J.; Sridharan, V.; Wilson, D. Tetrahedron Lett. 1994, 35, 7661-7664.
35. Wakita, Y.; Yasunaga, T.; Akita, M.; Kojima, M. J. Organomet. Chem. 1986, 301, C17-C20. Grigg, R.; Redpath, J.; Sridharan, V.; Wilson, D. Tetrahedron Lett. 1994, 35, 7661-7664.
36. Schlosser, M. J. Organomet. Chem. 1967, 8, 9-16. Schlosser, M. Mod. Synth. Methods 1992, 6, 227-271. Mordini, A. In Advances in Carbanion Chemistry; Snieckus, V., Ed.; JAI Press Inc.: Greenwich, CT, 1992; Vol. 1, pp 1-45. Schlosser, M.; Faigl, F.; Franzini, L.; Geneste, H.; Katsoulos, G.; Zhong, G. Pure Appl. Chem. 1994, 66, 1439-1446. Lochmann, L. Eur. J. Inorg. Chem. 2000, 1115-1126.
37. Schlosser, M. J. Organomet. Chem. 1967, 8, 9-16. Schlosser, M. Mod. Synth. Methods 1992, 6, 227-271. Mordini, A. In Advances in Carbanion Chemistry; Snieckus, V., Ed.; JAI Press Inc.: Greenwich, CT, 1992; Vol. 1, pp 1-45. Schlosser, M.; Faigl, F.; Franzini, L.; Geneste, H.; Katsoulos, G.; Zhong, G. Pure Appl. Chem. 1994, 66, 1439-1446. Lochmann, L. Eur. J. Inorg. Chem. 2000, 1115-1126.
38. Schlosser, M. J. Organomet. Chem. 1967, 8, 9-16. Schlosser, M. Mod. Synth. Methods 1992, 6, 227-271. Mordini, A. In Advances in Carbanion Chemistry; Snieckus, V., Ed.; JAI Press Inc.: Greenwich, CT, 1992; Vol. 1, pp 1-45. Schlosser, M.; Faigl, F.; Franzini, L.; Geneste, H.; Katsoulos, G.; Zhong, G. Pure Appl. Chem. 1994, 66, 1439-1446. Lochmann, L. Eur. J. Inorg. Chem. 2000, 1115-1126.
39. Schlosser, M. J. Organomet. Chem. 1967, 8, 9-16. Schlosser, M. Mod. Synth. Methods 1992, 6, 227-271. Mordini, A. In Advances in Carbanion Chemistry; Snieckus, V., Ed.; JAI Press Inc.: Greenwich, CT, 1992; Vol. 1, pp 1-45. Schlosser, M.; Faigl, F.; Franzini, L.; Geneste, H.; Katsoulos, G.; Zhong, G. Pure Appl. Chem. 1994, 66, 1439-1446. Lochmann, L. Eur. J. Inorg. Chem. 2000, 1115-1126.
40. Schlosser, M. J. Organomet. Chem. 1967, 8, 9-16. Schlosser, M. Mod. Synth. Methods 1992, 6, 227-271. Mordini, A. In Advances in Carbanion Chemistry; Snieckus, V., Ed.; JAI Press Inc.: Greenwich, CT, 1992; Vol. 1, pp 1-45. Schlosser, M.; Faigl, F.; Franzini, L.; Geneste, H.; Katsoulos, G.; Zhong, G. Pure Appl. Chem. 1994, 66, 1439-1446. Lochmann, L. Eur. J. Inorg. Chem. 2000, 1115-1126.
41. G. C. Fu and A. F. Littke have proved that triarylphosphines result in ineffective ligands in Suzuki cross-coupling of aryl chlorides (see ref 4).
42. +, 42), 135 (100), 77 (31), 69 (14), 63 (15), 41 (19).