156049-40-0Relevant articles and documents
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
Evoniuk, Christopher J.,Gomes, Gabriel Dos Passos,Ly, Michelle,White, Frankie D.,Alabugin, Igor V.
, p. 4265 - 4278 (2017/04/27)
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-preference for the cyclization processes.
Coupling cyclizations with fragmentations for the preparation of heteroaromatics: Quinolines from o-alkenyl arylisocyanides and boronic acids
Evoniuk, Christopher J.,Ly, Michelle,Alabugin, Igor V.
supporting information, p. 12831 - 12834 (2015/08/06)
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.
