Area of research
Organic Chemistry · Molecular Biology
Research interest
Research topics from publications: 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; 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. Representative work: Stereoelectronic restrictions on homoallylic ring expansion in alkyne cascades can be overcome by using alkenes as synthetic equivalents of alkynes in reaction cascades that are terminated by C-C bond fragmentation. Implementation of this approach using Mn(iii)-mediated reaction of o-alkenyl isocyanides and boronic acids leads to efficient synthesis of substituted quinolines Selective addition of radicals to isonitriles can be harnessed for initiating reaction cascades designed to overcome the stereoelectronic restrictions on homoallylic ring expansion in alkyne reactions and to develop a new general route for the preparation of N-heteroaromatics. This method utilizes alkenes as synthetic equivalents of alkynes by coupling homoallylic ring expansion to yield the formal "6-endo" products with aromatization via stereoelectronically assisted C-C bond scission. Computational analysis of the homoallyic expansion potential energy surface reveals that the indirect 5-exo/3-exo/retro-3-exo path is faster than the direct 6-endo-trig closure, revealing the general exo-pref
Coupling Radical Homoallylic Expansions with C–C Fragmentations for the Synthesis of Heteroaromatics: Quinolines from Reactions of <i>o</i>-Alkenylarylisonitriles with Aryl, Alkyl, and Perfluoroalkyl Radicals
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
Coupling cyclizations with fragmentations for the preparation of heteroaromatics: quinolines from o-alkenyl arylisocyanides and boronic acids
ChemInform Abstract: Coupling Cyclizations with Fragmentations for the Preparation of Heteroaromatics: Quinolines from O‐Alkenyl Arylisocyanides and Boronic Acids.