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. 2017 Oct 2;56(41):12774-12777.
doi: 10.1002/anie.201706799. Epub 2017 Aug 30.

Synthesis of Bicyclo[1.1.1]pentane Bioisosteres of Internal Alkynes and para-Disubstituted Benzenes from [1.1.1]Propellane

Ilya S Makarov  1 , Cara E Brocklehurst  2 , Konstantin Karaghiosoff  1 , Guido Koch  2 , Paul Knochel  1
Affiliations

Synthesis of Bicyclo[1.1.1]pentane Bioisosteres of Internal Alkynes and para-Disubstituted Benzenes from [1.1.1]Propellane

Ilya S Makarov et al. Angew Chem Int Ed Engl. .

Abstract

We report a general preparation of arylated bicyclo[1.1.1]pentanes through the opening of [1.1.1]propellane with various arylmagnesium halides. After transmetalation with ZnCl2 and Negishi cross-coupling with aryl and heteroaryl halides, bis-arylated bicyclo[1.1.1]pentanes are obtained. These bis-arylated bicyclo[1.1.1]pentanes may be considered as bioisosteres of internal alkynes. Bioisosteres of tazarotene and the metabotropic glutamate receptor 5 (mGluR5) antagonist 2-methyl-6-(phenylethynyl)pyridine were prepared and their physicochemical properties were evaluated.

Keywords: arenes; bioisosteres; magnesium; nitrogen heterocycles; small ring systems.

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