4,4,6-Trimethyl-2-vinyl-1,3,2-dioxaborinane: An efficient and selective 2-carbon building block for vinylboronate Suzuki-Miyaura coupling reactions

Synlett

Volumn , Issue 3, 2005, Pages 529-531

  Lightfoot, Andrew P ^a   Twiddle, Steven J R ^b   Whiting, Andrew ^b  

^a GLAXOSMITHKLINE   (United Kingdom)

^b DURHAM UNIVERSITY   (United Kingdom)

Author keywords

Chemoselectivity; Palladium(0); Suzuki Miyaura coupling; Vinylboronate ester

Indexed keywords

4,4,6 TRIMETHYL 2 VINYL 1,3,2 DIOXABORINANE; ALKADIENE; BORINIC ACID DERIVATIVE; CARBON; HALIDE; PALLADIUM; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; STEREOCHEMISTRY; SUZUKI REACTION; SYNTHESIS;

EID: 14644442284     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-862354     Document Type: Article

References (20)

1. Thirsk, C.; Whiting, A. J. Chem. Soc., Perkin Trans. 1 2002, 8, 999.
2. (a) Omura, S.; Tanaka, Y.; Kanaya, I.; Shinose, M.; Takahashi, Y. J. Antibiot. 1990, 43, 1034.
3. (b) Henaff, N.; Whiting, A. Org. Lett. 1999, 1, 1137.
4. (c) Henaff, N.; Whiting, A. Tetrahedron 2000, 56, 5193.
5. (a) Hunt, A. R.; Stewart, S. K.; Whiting, A. Tetrahedron Lett. 1993, 34, 3599.
6. (b) Stewart, S. K.; Whiting, A. J. Organomet. Chem. 1994, 482, 293.
7. (c) Stewart, S. K.; Whiting, A. Tetrahedron Lett. 1995, 36, 3925.
8. (a) Nakagawa, M.; Furihata, K.; Hayakawa, Y.; Seto, H. Tetrahedron Lett. 1991, 32, 659.
9. (b) Hasegawa, T.; Kamiya, T.; Henmi, T.; Iwasaki, H.; Yamatodani, S. J. Antibiot. 1975, 28, 167.
10. (c) Nakagawa, M.; Toda, Y.; Furihata, K.; Hayakawa, Y.; Seto, H. J. Antibiot. 1992, 45, 1133.
11. Lightfoot, A. P.; Maw, G.; Thirsk, C.; Twiddle, S. J. R.; Whiting, A. Tetrahedron Lett. 2003, 44, 7645.
12. (a) Lando, V. R.; Monteiro, A. L. Org. Lett. 2003, 5, 2891.
13. (b) Molander, G. A.; Rivero, M. R. Org. Lett. 2002, 4, 107.
14. (c) Molander, G. A.; Bernardi, C. R. J. Org. Chem. 2002, 67, 8424.
15. 1H NMR analysis to determine the Heck: Suzuki ratio, which was carried out after evaporation to give the crude product. Purification was carried out by silica gel column chromatography (hexane as eluant).
16. Uenishi, J.; Beau, J.; Armstrong, R. W.; Kishi, Y. J. Am. Chem. Soc. 1987, 109, 4756.
17. Characterization data for products 8a-e, 8h and 10 was consistent with commercial samples. See: (a) 8f: Lebel, H. V.; Paquet, V. Organometallics 2004, 23, 1187.
18. (b) 8g: Chinkov, N.; Majumdar, S.; Marek, I. J. Am. Chem. Soc. 2002, 124, 10282.
19. Tinnemans, A. H. A.; Laarhoven, W. H. J. Chem. Soc., Perkin Trans. 2 1976, 10, 1104.
20. Miyaura, N. J. Organomet. Chem. 2002, 653, 54.