Synthesis of Monofluoroalkenes through Visible-Light-Promoted Defluorinative Alkylation of gem-Difluoroalkenes with 4-Alkyl-1,4-dihydropyridines

• DOI: 10.1021/acs.orglett.0c00134
• Publication Date: 2020-01-28T12:36:15Z
• Authors: Hai-Wu Du; Jing Sun; Qi-Sheng Gao; Jing-Yun Wang; He Wang; Zhaoqing Xu; Ming-Dong Zhou
• Keywords: 01 natural sciences; 0104 chemical sciences

In this study, a facile and efficient method to synthesize monofluoroalkenes by photoredox catalytic defluorinative alkylation of gem-difluoroalkenes with 4-alkyl-1,4-dihydropyridines under mild conditions (room temperature) is described. This novel strategy is applicable for a broad range of gem-difluoroalkene substrates with good functional group tolerance and a variety of 4-alkyl-1,4-dihydropyridines (including primary, secondary, and even tertiary alkyl radicals). Moreover, it also allows the challenging radical coupling with glycosyl-based 4-alkyl-1,4-dihydropyridines (DHPs) to synthesize monofluoroalkenylated saccharides.