Palladium-catalysed couplings of difluoroenol carbamate derivatives

Synlett

Volumn , Issue 7, 2000, Pages 963-966

  DeBoos, Gareth A ^a   Fullbrook, Jeremy J ^b   Owton, W Martin ^c   Percy, Jonathan M ^b   Thomas, Andrew C ^b  

^a Avecia Biologics Limited   (United Kingdom)

^b UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^c ELI LILLY AND COMPANY   (United States)

Author keywords

Difluoroalkenes; Difluoroketones; Palladium; Stille; Suzuki Miyaura

Indexed keywords

CARBAMIC ACID DERIVATIVE; PALLADIUM;

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

EID: 0033930179     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (20)

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2. (b) Davis, C. R.; Burton, D. J. Tetrahedron Lett. 1996, 37, 7237.
3. (c) Lu, L.; Burton, D. J. Tetrahedron Lett. 1997, 38, 7673.
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9. (b) Howarth, J. A.; Owton, W. M.; Percy, J. M.; Rock, M. H. Tetrahedron 1995, 51, 10289 describes preparations of 1a-c in full.
10. (c) For examples of copper(I)-mediated substitutions, see Crowley, P. J.; Howarth, J. A.; Owton, W. M.; Percy, J. M.; Stansfield, K. Tetrahedron Lett. 1996, 37, 5975.
11. Farina, V.; Krishanmurthy, V.; Scott, W. J. The Stille Reaction; J. Wiley and Sons: New York 1998.
12. Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59 5905.
13. 19F) and MS data.
14. Miyaura, N.; Suzuki, A. Chem Rev. 1995, 95, 2457. One cited example has a chlorine atom a-to the C-Pd bond: Yoshida, T.; Okano, T.; Otsuka, S. J. Chem. Soc., Dalton Trans. 1976, 99.
15. Miyaura, N.; Suzuki, A. Chem Rev. 1995, 95, 2457. One cited example has a chlorine atom a-to the C-Pd bond: Yoshida, T.; Okano, T.; Otsuka, S. J. Chem. Soc., Dalton Trans. 1976, 99.
16. The reactive Pd(II) complex with only two phosphine ligands was used toarylatea vinyl bromide; see Johnson, C. R.; Johns, B. A. J. Org. Chem. 1997, 62, 6046.
17. 2: C 61.16%, H 5.93%, N 5.49%. Found C 60.89%, H 5.99%, N 5.31%.
18. Watanabe, T.; Miyaura, N.; Suzuki, A. Synlett 1992, 207.
19. Derwing, C.; Hoppe, D. Synthesis 1996, 149.
20. For an application of this carbamate for the synthesis of difluorinated polyols, see Balnaves, A. S.; Palmer, M. J.; Percy, J. M. Chem. Commun. 1999, 2183.