Synthesis of Novel Fluorinated Benzofurans and Dihydrobenzofurans

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Georg Thieme Verlag

Abstract

Starting from easily accessible propargylic fluorides an intramolecular oxa-Michael addition affords, in good yields, new gem-difluo-rodihydrobenzofurans bearing an electrophilic double bond in position 2. On these intermediates nucleophilic additions and Diels-Alder reactions have been performed affording functionalized fluorinated dihydrobenzofurans. On the other hand, Pd-catalyzed defluorinations give the corresponding fluorine containing benzofurans. © Georg Thieme Verlag Stuttgart · New York-Synlett 2017.

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2,3-dihy-drobenzofurans, Benzofurans, Fluorine, Gem-difluoropropargyls, Heterocycles, Oxa-michael additions, Benzofuran derivative, Dihydrobenzofuran derivative, Fluoride, Methyl 2 (3 fluoro 5 phenylbenzofuran 2 yl)acetate, Methyl 2 (3,3 difluorobenzofuran 2(3h) ylidene)acetate, Methyl 2 (5 bromo 3 fluorobenzofuran 2 yl)acetate, Methyl 2 (5 bromo 3,3 difluoro 2 hydroxy 2,3 dihydrobenzofuran 2 yl)acetate, Methyl 2 (5 bromo 3,3 difluorobenzofuran 2(3h) ylidene)acetate, Methyl 2 [3 fluoro 5 (prop 1 en 2 yl)benzofuran 2 yl]acetate, Methyl 2 [5 bromo 3,3 difluoro 2 (2 hydroxyethylthio) 2,3 dihydrobenzofuran 2 yl]acetate, Unclassified drug, Catalysis, Chemical bond, Chemical structure, Defluorination, Diels alder reaction, Fluorination, Michael addition, Nucleophilicity, Review, Synthesis

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