… And Alcohols Pair With Alkenes | Chemical & Engineering News
Volume 89 Issue 38 | p. 29 | Concentrates
Issue Date: September 19, 2011

… And Alcohols Pair With Alkenes

Water is the sole byproduct of new carbon-carbon bond formation
Department: Science & Technology
Keywords: catalysis, organometallic chemistry, cross coupling
This alkene-alcohol coupling forges a new carbon-carbon bond.
Ru catalyst
This alkene-alcohol coupling forges a new carbon-carbon bond.

Using a ruthenium catalyst, chemists have combined alkenes and alcohols to form new carbon-carbon bonds (Science, DOI: 10.1126/sci ence.1208839). The method couples two of the most abundant types of chemical feedstocks and forms water as the sole by-product. Even though alcohols are inexpensive, they aren’t used as alkylating agents in workhorse C–C bond-forming reactions such as the Heck reaction because they undergo side reactions, including dehydrogenation. But Chae S. Yi and colleagues at Marquette University found a cationic ruthenium complex that coaxes a variety of alcohols to undergo the challenging carbon-oxygen bond cleavage step needed to perform the alkylation. The new reaction is gentle to richly functionalized bioactive alkenes such as strychnine, leaving most functional groups and chiral centers intact. The process “has great potential for building up complexity in an efficient and waste-free manner,” says Vy M. Dong, who studies C–H bond functionalization at the University of Toronto. She notes that in some cases the reaction yields mixtures of products, but thinks it would be interesting to explore alternative ligands for the ruthenium catalyst to better control selectivity.

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