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
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.
Evoniuk, Christopher J.,Gomes, Gabriel Dos Passos,Ly, Michelle,White, Frankie D.,Alabugin, Igor V.
p. 4265 - 4278
(2017/04/27)
Coupling cyclizations with fragmentations for the preparation of heteroaromatics: Quinolines from o-alkenyl arylisocyanides and boronic acids
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.
Evoniuk, Christopher J.,Ly, Michelle,Alabugin, Igor V.
supporting information
p. 12831 - 12834
(2015/08/06)
Synthetic utility of propylphosphonic anhydridedmso media: An efficient one-pot three-component synthesis of 2-arylquinolines
Propylphosphonic anhydride (T3P?)DMSO-mediated onepot three-component synthesis which provides 2-arylquinolines in a single step from benzyl alcohols, anilines, and ethyl vinyl ether by the modified Povarov reaction has been demonstrated. T3P?DMSO is a mild and low-toxic peptide coupling agent and an easy to handle reagent for bulk reactions at room temperature.
Narasimhamurthy, Kereyagalahally H.,Chandrappa, Siddappa,Kumar, Kothanahally S. Sharath,Swaroop, Toreshettahally R.,Rangappa, Kanchugarakoppal S.
supporting information
p. 1073 - 1075
(2013/09/24)
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