Home Products Cited in Publications Worldwide Investigations into Alcohol Functionalization via Barton-McCombie Type Deoxygenation
University of North Carolina,2023.
Chufan Andrew Jin
Reactive species that are employed as electrophiles in functionalization of substrates are typically prepared from native functionality such as alcohols and carboxylic acids. The addition of a pre-functionalization step of native substrates can reduce the efficiency of syntheses. These pre-functionalization reactions along with the functionalization reactions themselves proceed through polar mechanisms, limiting the scope of both functionalization and pre-functionalization reactions. Reported herein are preliminary efforts in the development of a deoxy-functionalization protocol for secondary and tertiary alcohols. The reported protocol proceeds through a derived Barton-McCombie deoxygenation mediated by a super silyl radical. Transfer of a thiocarbonate activating group to the silyl radical generates carbon radical which can be trapped out with an external sulfonyl trap, generating sulfonyl radical, which may then react with an allylic silane allowing for turnover of the radical chain.