1. Selective Catalytic C-H Alkylation of Alkenes with Alcohols.
- Author
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Lee, Dong-Hwan, Kwon, Ki-Hyeok, and Yi, Chae S.
- Subjects
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ALKYLATION , *ALKENES , *ALCOHOLS (Chemical class) , *ALKYNES , *CATIONS , *FEEDSTOCK , *ELECTROPHILES - Abstract
Alkenes and alcohols are among the most abundant and commonly used organic feedstock in industrial processes. We report a selective catalytic alkylation reaction of alkenes with alcohols that forms a carbon-carbon bond between vinyl carbon-hydrogen (C-H) and carbon-hydroxy centers with the concomitant loss of water. The cationic ruthenium complex [(C6H6)(PCy3)(C0)RuH]+BF4- (Cy, cyclohexyl) catalyzes the alkylation in solution within 2 to 8 hours at temperatures ranging from 75° to 110°C and tolerates a broad range of substrate functionality, including amines and carbonyls. Preliminary mechanistic studies are inconsistent with Friedel-Crafts-type electrophilic activation of the alcohols, suggesting instead a vinyl C-H activation pathway with opposite electronic polarization. [ABSTRACT FROM AUTHOR]
- Published
- 2011
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