Ni-Catalyzed Cross Coupling of Alkoxide-Containing Vinyl Halides with Grignard Reagents. A "One-Pot" Synthesis of 2-[(Trimethylsilyl)methyl]-2-propen-1-yl Acetate

Journal of Organic Chemistry

Volumn 62, Issue 5, 1997, Pages 1523-1526

  Organ, Michael G ^a   Murray, Aaron P ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0008427626     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961900u     Document Type: Article

References (29)

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2. For general discussions regarding transition metal coordinating affinity, see: (a) Crabtree, R. H. The Organometallic Chemistry of the Transition Metals; Wiley: New York, 1994; pp 44-139. (b) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987; pp 57-278.
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4. For selective catalytic hydrogenation of multiple bonds, see: (a) Evans, D. A.; Morrissey, M. M. J. Am. Chem. Soc. 1984, 106, 3866-3868. (b) Thompson, H. W.; Naipawer, R. E. J. Am. Chem. Soc. 1973, 95, 6379-6386.
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12. Compounds 8a and 8b were prepared as indicated in the following equation using well established chemistry: Equation Presented
13. 3 (Luche reduction, see: Germal, A. L.; Luche, J.-L. J. Am. Chem. Soc. 1981, 103, 5454) with the corresponding 2-halocyclohex-2-en-1-one, which generally proceeds with quantitative recovery. These precursors were prepared following the method of Johnson; see: Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W.; Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron Lett. 1992, 33, 917-918.
14. 3 (Luche reduction, see: Germal, A. L.; Luche, J.-L. J. Am. Chem. Soc. 1981, 103, 5454) with the corresponding 2-halocyclohex-2-en-1-one, which generally proceeds with quantitative recovery. These precursors were prepared following the method of Johnson; see: Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W.; Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron Lett. 1992, 33, 917-918.
15. Compound 12 was prepared as indicated in the following equation: Equation Presented
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