Activation of sp3-hybridized Carbon-Hydrogen Bonds for the Formation of New Carbon-Carbon Bonds

Abstract

By Nathan Ranly, Chemistry-ACS; Alyssa Solano, Biochemistry

Advisor: Allan Pinhas

Presentation ID: PM_D26

Abstract: The formation of new carbon-carbon bonds from sp3-hybridized carbon-hydrogen bonds is one of the greatest, yet most rewarding, challenges in organic chemistry; a robust, effective method of activating carbon-hydrogen bonds would be valuable to a wide range of chemical syntheses. Many existing techniques require expensive metal catalysts, toxic reagents, and/or produce significant waste. In contrast, Fenton's reagent, a mixture of iron(II) and hydrogen peroxide and commonly used to decompose large organic molecules, is a low toxicity potential alternative, producing only water and rust as byproducts. In this research, the effectiveness, limitations, and selectivity of Fenton's reagents for the formation of new carbon-carbon bonds are investigated. High selectivity at the beta carbon and consistency in product yields have been observed in the coupling of triethylamine. Additionally, the cross-coupling of triethylamine with acetonitrile, acetone, and ethyl acetate has been investigated. This technique has also been applied to other functional groups, namely ethers and esters. Of note, tetrahydrofuran, in contrast to the beta coupling of the amine, has been found to couple selectively at the carbon in the alpha position to the oxygen atom.