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Volumn 54, Issue 7, 1989, Pages 1502-1505

Palladium-Catalyzed Vinylation of Alkyl Vinyl Ethers with Enol Triflates. A Convenient Synthesis of 2-Alkoxy 1,3-Dienes

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EID: 0000104277     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00268a006     Document Type: Article
Times cited : (57)

References (38)
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    • Diels-Alder reactions of heterosubstituted dienes have been reviewed: (a) Petrzilka, M.; Grayson, J. I. Synthesis 1983, 753. (b) Schmidt, R. R. Acc. Chem. Res. 1986,19, 250. For an excellent theoretical survey, see: (c) Kahn, S. D.; Pau, C. F.; Overman, L. E.; Hehre, W. J. J. Am. Chem. Soc. 1986, 108, 7381.
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    • For some examples employing 2-alkoxy dienes, see: (a) (b) Caine, D.; Harrison, C. H.; VanDerveer, D. G. ACS Monograph 180 1983, 24, 1353. (c) Rao, A. V. R.; Deshpande, V. H.; Reddy, N. L. 1980, 21, 2661. (d) Lebouc, A.; Delaunay, J.: Riobe. 0. J. Chem. Res. M 1980. 2683.
    • For some examples employing 2-alkoxy dienes, see: (a) Pindur, U.; Pfeuffer, L. Tetrahedron Lett. 1987, 28, 3079. (b) Caine, D.; Harrison, C. H.; VanDerveer, D. G. ACS Monograph 180 1983, 24, 1353. (c) Rao, A. V. R.; Deshpande, V. H.; Reddy, N. L. Tetrahedron Lett. 1980, 21, 2661. (d) Lebouc, A.; Delaunay, J.: Riobe. 0. J. Chem. Res. M 1980. 2683.
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    • A recent report from Stilles group demonstrated a palladium-catalyzed vinylation of the enol ether 2,3-dihydro-4H-pyran starting from a vinyl triflate. This process furnished a 1,6-diene as a result of double bond migration
    • A recent report from Stilles group demonstrated a palladium-catalyzed vinylation of the enol ether 2,3-dihydro-4H-pyran starting from a vinyl triflate. This process furnished a 1,6-diene as a result of double bond migration: Scott, W. J.; Pena, M. R.; Sward, K.; Stoessel, S. J.; Stille, J. K. J. Org. Chem. 1985, 50, 2302.
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    • Principles and Applications of Organotransition Metal Chemistry
    • For general discussions of these reactions, see: (a) 2nd ed.; Chapter 14:4. (b) Negishi, E.; Takahashi, T.; Baba, S.; Van Horn, D. E.; Okukado, N. J. Am. Chem. Soc. 1987, 109, 2393. (c) Negishi, E.; Takahashi, T.; Akiyoshi, K. In Catalysis of Organic Reactions; Rylander, P. N., Greenfield, H., Augustine, R. L., Eds.; Marcel Decker: New York, 1988.
    • For general discussions of these reactions, see: (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry, 2nd ed.; University Science Books: Mill Valley, 1987; Chapter 14:4. (b) Negishi, E.; Takahashi, T.; Baba, S.; Van Horn, D. E.; Okukado, N. J. Am. Chem. Soc. 1987, 109, 2393. (c) Negishi, E.; Takahashi, T.; Akiyoshi, K. In Catalysis of Organic Reactions; Rylander, P. N., Greenfield, H., Augustine, R. L., Eds.; Marcel Decker: New York, 1988.
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    • These starting materials were introduced fairly recently and are particularly attractive because of their simple preparation. The applications of triflates in organometallic chemistry were reviewed recently
    • These starting materials were introduced fairly recently and are particularly attractive because of their simple preparation. The applications of triflates in organometallic chemistry were reviewed recently: Scott, W. J.; McMurry, J. E. Acc. Chem. Res. 1988, 21, 47.
    • (1988) Acc. Chem. Res. , vol.21 , pp. 47
    • Scott, W.J.1    McMurry, J.E.2
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    • Coupling with halides: (a) With triflates: (b) Scott, W. J.; Stille, J. K J. Am. Chem. Soc. 1986, 108, 3033.
    • Coupling with halides: (a) Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813. With triflates: (b) Scott, W. J.; Stille, J. K J. Am. Chem. Soc. 1986, 108, 3033.
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    • Stille, J.K.1    Groh, B.L.2
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    • (b) Hallberg, A.; Westfelt, L.; Holm, B. Synth. Commun. 1981, 46, 5414.
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    • Facile oxidative cleavage of some enol ethers with atmospheric oxygen is known, see
    • Facile oxidative cleavage of some enol ethers with atmospheric oxygen is known, see: Taylor, R. J. Chem. Res. S 1987, 178.
    • (1987) J. Chem. Res. S , pp. 178
    • Taylor, R.1


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