Faculty Collaboration Database

Selective catalytic C-H alkylation of alkenes with alcohols. Science 2011 Sep 16;333(6049):1613-6

Date

09/17/2011

Pubmed ID

21921195

DOI

10.1126/science.1208839

Scopus ID

2-s2.0-80052945833 (requires institutional sign-in at Scopus site)   176 Citations

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 [(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° 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.

Author List

Lee DH, Kwon KH, Yi CS

Author

Chae Yi PhD Professor, Inorganic and Organometallic Chemistry, Homogeneous Catalysis in the Chemistry department at Marquette University