Hydrogen Bond Directed Photocatalytic Hydrodefluorination: Overcoming Electronic Control.

ABSTRACT: The photocatalytic C-F functionalization of highly fluorinated arenes is a powerful method for accessing functionalized multifluorinated arenes. The decisive step in the determining regioselectivity in fluorine functionalization is fluoride fragmentation from the radical anion of the multifluorinated arene. To date, the availability of regioisomers has been dictated by the innate electronics of the fluorinated arene, limiting the synthetic utility of the chemistry. This study investigates the remarkable ability of a strategically located hydrogen bond to transcend the normal regioselectivity of the C-F functionalization event. A significant rate acceleration is additionally observed for hydrodefluorination of fluorines that can undergo intramolecular hydrogen bonds that form 5-8-membered c

SUBMITTER: Khaled MB 

PROVIDER: S-EPMC6069595 | biostudies-literature | 2017 Sep

REPOSITORIES: biostudies-literature