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United States Department of Agriculture

Agricultural Research Service

Research Project: CHEMICAL SIGNALS FOR MANAGING INSECTS Title: An efficient copper-catalyzed cross-coupling reaction of alkyl-triflates with alkyl-Grignard reagents

Authors
item Wang, Shifa - VPI & STATE UNIV.
item Zhang, Aijun

Submitted to: Organic Preparation Proceeds International
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: February 9, 2008
Publication Date: June 17, 2008
Citation: Wang, S., Zhang, A. 2008. An improved copper-catalyzed cross-coupling reaction of alkyl-triflates with primary alkyl-Grignard reagents. Org. Prep. Interntl. Journal of Organic Chemistry. 40:293-301.

Interpretive Summary: Organic chemical components are often used as building blocks by scientists to make larger molecules which have valuable chemical properties. For example, scientists make synthetic insect pheromone chemicals, which attract other insects and can be used to control insects and decrease damage. But it is often expensive to produce these organic chemical building blocks, and it takes a lot of time. We developed this efficient method which should make many organic compounds easily accessible to the scientists and industries for the preparation of pheromone components in the laboratory and industry.

Technical Abstract: A highly efficient method for the formation of C-C covalent bonds by cross-coupling reaction between alkyl-triflates and alkyl-Grignard reagents catalyzed by copper catalyst, Li2CuCl4, is described. The reaction works with most primary triflates in diethyl ether at low temperature within 0.5-3 h and resulting coupling products are usually in >90% isolated yields. For the secondary and hindered primary triflates, the higher reaction temperature and longer reaction time are usually required in order to get the comparable yields.

Last Modified: 8/22/2014
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