A new flexible strategy for the synthesis of gem-difluoro-bisarylic derivatives and heterocyclic analogues |
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| Authors: | Ali Khalaf Danielle GréeHassan Abdallah Nada JaberAli Hachem René Grée |
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| Institution: | a Université de Rennes 1, Laboratoire Sciences Chimiques de Rennes, CNRS UMR 6226, Avenue du Général Leclerc, 35042 Rennes Cedex, France
b Laboratory for Medicinal Chemistry and Natural Products, Lebanese University, Faculty of Sciences (I) and PRASE-EDST, Hadath, Beyrouth, Lebanon |
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| Abstract: | A new strategy has been designed for the preparation of gem-difluoro-bisarylic derivatives. It starts from easily accessible and reactive gem-difluoro-propargylic intermediates and elaborates the aromatic rings by a Diels-Alder-aromatization sequence. Heterocyclic systems can be also obtained by 1,3 dipolar cycloadditions, affording mixed aromatic/heteroaromatic derivatives with CF2 as a linker. Since this motif is a bioisostere of O and CO, corresponding bisarylic scaffolds could be of use to prepare chemical libraries of fluorinated analogues of bioactive natural products and/or drugs. |
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| Keywords: | Propargylic fluorides gem-Difluoro compounds Cycloaddition reactions gem-Difluoro-bisaryl derivatives Fluorinated linkers |
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