Synthesis of an elusive, stable 2-azaallyl radical guided by electrochemical and reactivity studies of 2-azaallyl anions.

ABSTRACT: The super electron donor (SED) ability of 2-azaallyl anions has recently been discovered and applied to diverse reactivity, including transition metal-free cross-coupling and dehydrogenative cross-coupling processes. Surprisingly, the redox properties of 2-azaallyl anions and radicals have been rarely studied. Understanding the chemistry of elusive species is the key to further development. Electrochemical analysis of phenyl substituted 2-azaallyl anions revealed an oxidation wave at E _1/2 or E _pa = -1.6 V versus Fc/Fc⁺, which is ∼800 mV less than the reduction potential predicted (E _pa = -2.4 V vs. Fc/Fc⁺) based on reactivity studies. Investigation of the kinetics of electron transfer revealed reorga

SUBMITTER: Panetti GB 

PROVIDER: S-EPMC8179533 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature