Selective Catalytic C–H Alkylation of Alkenes with Alcohols

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Science  16 Sep 2011:
Vol. 333, Issue 6049, pp. 1613-1616
DOI: 10.1126/science.1208839

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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)(CO)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.

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