An efficient synthesis of 1,4‐disubstituted and 1,4,5‐trisubstituted 1,2,3‐triazole from α,α‐difluoro‐N‐tosylhydrazone and amine through a C−F bond cleavage protocol has been developed. α,α‐Difluoro‐N‐tosylhydrazone is used as a new reagent, which can transform amines to 1,2,3‐triazoles with high efficiency and excellent functional group compatibility without using transition‐metal catalysts, azide reagents and oxidants.
Fluorine-containing b-amino acids and their derivatives have attracted significant attention due to their importance in life sciences.H erein the previously unknown difluoroketenimine,t he analogue of the elusive difluoroketene,h as been generated by the reaction of difluorocarbene and isocyanide,w hich further undergoes [2+ +2] cycloaddition with imine.T he three-component reaction affords a,adifluoro-b-amino amides in good yields.M echanistic studies reveal the unique properties of the difluoroketenimine in the [2+ +2] cycloaddition with imine. Scheme 1. Staudinger synthesis and proposed [2+ +2] cycloaddition with difluoroketenimine.Theauthors declare no conflict of interest. Scheme 5. Proposed pathways for [2+ +2] cycloaddition. Scheme 6. Evaluation of electronic effects with Hammett linear free energy correlation.
Palladium-catalyzed cross-coupling reactions of N-tosylhydrazones and arylbromides have been applied for the first time in the synthesis of cross-conjugated polymers, namely poly(arylene-1,1-vinylidene)s (iso-PAVs).
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