Christopher J. Evoniuk

Area of research

Organic Chemistry · Materials Chemistry

Research interest

Research topics from publications: Alkenes as Alkyne Equivalents in Radical Cascades Terminated by Fragmentations: Overcoming Stereoelectronic Restrictions on Ring Expansions for the Preparation of Expanded Polyaromatics; Coupling N–H Deprotonation, C–H Activation, and Oxidation: Metal-Free C(sp3)–H Aminations with Unprotected Anilines; Coupling cyclizations with fragmentations for the preparation of heteroaromatics: quinolines from o-alkenyl arylisocyanides and boronic acids; Coupling Radical Homoallylic Expansions with C–C Fragmentations for the Synthesis of Heteroaromatics: Quinolines from Reactions of o-Alkenylarylisonitriles with Aryl, Alkyl, and Perfluoroalkyl Radicals; Testing the limits of radical-anionic CH-amination: a 10-million-fold decrease in basicity opens a new path to hydroxyisoindolinesviaa mixed C–N/C–O-forming cascade; Double C–H amination by consecutive SET oxidations; Changing the path of least resistance, or access to endo-dig products via a sequence of three exo-trig transition states: electronic effects in homoallyic ring expansion cascades of alkenyl isonitriles; ChemInform Abstract: Coupling Cyclizations with Fragmentations for the Preparation of Heteroaromatics: Quinolines from O‐Alkenyl Arylisocyanides and Boronic Acids; ChemInform Abstract: Double C—H Amination by Consecutive SET Oxidations; Diverting Radical-Anionic C-H Amidation to a C-N/C-O Cascade for the Construction of Hydroxyisoindolines from Unprotected Amides. Representative work: Chemoselective interaction of aromatic enynes with Bu3Sn radicals can be harnessed for selective cascade transformations, yielding either Sn-substituted naphthalenes or Sn-indenes. Depending on the substitution at the alkene terminus, the initial regioselective 5-exo-trig cyclizations can be intercepted at the 5-exo stage via either hydrogen atom abstraction or C-S bond scission or allowed to proceed further to the formal 6-endo products via homoallylic ring expansion. Aromatization of the latter occurs via β-C-C bond scission, which is facilitated by 2c,3e through-bond interactions, a new stereoelectronic effect in radical chemistry. The combination of formal 6-endo-trig cyclization with st An intramolecular oxidative C(sp3)–H amination from unprotected anilines and C(sp3)–H bonds readily occurs under mild conditions using t-BuOK, molecular oxygen and N,N-dimethylformamide (DMF). Success of t

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