Synthesis of 1-Azabicyclo[2.1.1]hexanes via Formal Single Electron Reduction of Azabicyclo[1.1.0]butanes under Photochemical Conditions.

Zanini, Margherita; Noble, Adam; Aggarwal, Varinder K

Zanini, Margherita; Noble, Adam; Aggarwal, Varinder K.

Afiliación

Zanini M; School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS.
Noble A; School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS.
Aggarwal VK; School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS.

Angew Chem Int Ed Engl ; 63(44): e202410207, 2024 Oct 24.

Article en En | MEDLINE | ID: mdl-39038230

ABSTRACT

ABSTRACT

C(sp3)-rich heterocycles are privileged building blocks for pharmaceuticals and agrochemicals. Therefore, synthetic methods that provide access to novel saturated nitrogen-containing heterocycles are in high demand. Herein, we report a general synthesis of 1-azabicyclo[2.1.1]hexanes (1-aza-BCH) via a formal cycloaddition of azabicyclo[1.1.0]butanes (ABB) with styrenes under photochemical conditions. To overcome the challenging direct single electron reduction of ABBs, we designed a polar-radical-polar relay strategy that leverages a fast acid-mediated ring-opening of ABBs to form bromoazetidines, which undergo efficient debrominative radical formation to initiate the cycloaddition reaction. The reaction is applicable to a broad range of ABB-ketones and we demonstrate the 1-aza-BCH products can be further functionalized to access larger saturated, conformationally rigid heterocycles.

Palabras clave

1-Azabicyclo[2.1.1]hexanes; Bicyclo[1.1.0]butanes; Photoredox catalysis; Strained molecules; heterocycles

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2024 Tipo del documento: Article Pais de publicación: Alemania

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