A convenient synthesis of acylsilanes via hydroboration-oxidation of silylacetylenes

Synthesis (Germany)

Volumn 1981, Issue 4, 1981, Pages 288-289

  Miller, Joseph A ^a   Zweifel, George ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84989515507     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-1981-29419     Document Type: Short Survey

References (17)

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12. A. Hassner, J. Soderquist, J. Organomet. Chem. 131, C 1 (1977).
13. G. Zweifel, S. J. Backlund, J. Am. Chem. Soc. 99, 3184 (1977).
14. The vinylborane derived from 1-hexynyltrimethylsilane and disiamylborane, on oxidation with alkaline hydrogen peroxide utilizing a potassium carbonate-buffered medium, provided the corresponding acylsilane 3a in 68% yield.
15. Using the dichloroborane procedure, the acylsilanes were obtained in 24-40% yields based on the silylacetylenes 1 used5.
16. The stereochemistry of the enol borinates 5 has not yet been determined.
17. Anhydrous trimethylamine oxide was prepared from the commercially available dihydrate by azeotropic distillation with toluene.