Back to projects

Formation and Decomposition Products of Alkylated Hypervalent Iodine

  • Team: Faiz Ahmed, Cyrus Mowdawalla, Loma Dave, Grace Kim, Tian Li, Kiet Pham
  • Goal:The goal of this project is to develop a novel reaction methodology that uses hypervalent iodine to avoid β-hydride elimination; a detrimental side reaction that plagues current Pd-catalyzed cross-coupling methods.
  • Summary: The formation of carbon-carbon bonds are an active research interest in the synthetic community, but many methods have problems when trying to couple two different sp3 hybridized carbon atoms. The most common difficulty encountered is the propensity of sp3 carbons to undergo β-hydride elimination thus shutting down the catalytic process and creating side-products. The method proposed in this porject uses a completely unexplored approach by exploiting the metal-like properties and hypernucleofugality of hypervalent iodine. The uniqueness of the proposed reactions have several advantages over current methodology and the novel mechanism could be of considerable interest to other coupling systems. By using hypervalent iodine and soft metal alkyl transfer reagents, such as azastannatranes or boron reactants, an alkylated iodonium intermediate can be formed. The alkylated iodonium is then attacked with a hard metal alkylide to form the desired C(sp3)-C(sp3) coupling.