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

2017; Wiley; Volume: 56; Issue: 41 Linguagem: Inglês

10.1002/anie.201706799

1521-3773

Ilya S. Makarov, Cara E. Brocklehurst, Konstantin Karaghiosoff, Guido Koch, Paul Knochel,

Oxidative Organic Chemistry Reactions

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.