Selective Catalytic C-H Alkylation of Alkenes with Alcohols

作者：Lee Dong Hwan; Kwon Ki Hyeok; Yi Chae S^*

来源：Science, 2011, 333(6049): 1613-1616.

DOI：10.1126/science.1208839

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 [(C(6)H(6))(PCy(3))(CO)RuH](+)BF(4)(-) (Cy, cyclohexyl) catalyzes the alkylation in solution within 2 to 8 hours at temperatures ranging from 75 degrees to 110 degrees 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.

• 出版日期2011-9-16