An organocatalytic method for the modular synthesis of diverse N-aryl and N-alkyl azaheterocycles (indoles, oxindoles, benzimidazoles, and quinoxalinediones) is reported. The method employs a small-ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane P-oxide) and a hydrosilane reductant to drive the conversion of ortho-functionalized nitroarenes into azaheterocycles through sequential intermolecular reductive C-N cross coupling with boronic acids, followed by intramolecular cyclization. This method enables the rapid construction of azaheterocycles from readily available building blocks, including a regiospecific approach to N-substituted benzimidazoles and quinoxalinediones.
An organocatalytic method for the modular synthesis of diverse N-aryl and N-alkyl azaheterocycles (n class="Chemical">indoles, oxindoles, benzimidazoles, and quinoxalinediones) is reported. The method employs a small-ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane P-oxide) and a hydrosilane reductant to drive the conversion of ortho-functionalized nitroarenes into azaheterocycles through sequential intermolecular reductive C-N cross coupling with boronic acids, followed by intramolecular cyclization. This method enables the rapid construction of azaheterocycles from readily available building blocks, including a regiospecific approach to N-substituted benzimidazoles and quinoxalinediones.
Authors: Emma E Coyle; Bryan J Doonan; Andrew J Holohan; Killian A Walsh; Florie Lavigne; Elizabeth H Krenske; Christopher J O'Brien Journal: Angew Chem Int Ed Engl Date: 2014-09-22 Impact factor: 15.336
Authors: Alexandria P Taylor; Ralph P Robinson; Yvette M Fobian; David C Blakemore; Lyn H Jones; Olugbeminiyi Fadeyi Journal: Org Biomol Chem Date: 2016-07-12 Impact factor: 3.876
Authors: Yi-Chun Lin; Emmanuel Hatzakis; Sean M McCarthy; Kyle D Reichl; Ting-Yi Lai; Hemant P Yennawar; Alexander T Radosevich Journal: J Am Chem Soc Date: 2017-04-18 Impact factor: 15.419
Authors: Gen Li; Trevor V Nykaza; Julian C Cooper; Antonio Ramirez; Michael R Luzung; Alexander T Radosevich Journal: J Am Chem Soc Date: 2020-03-25 Impact factor: 15.419