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通过可见光促进的α,α-二氟烯烃与4-烷基-1,4-二氢吡啶的脱氟烷基化反应合成单氟烯烃

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

作者信息

Du Hai-Wu, Sun Jing, Gao Qi-Sheng, Wang Jing-Yun, Wang He, Xu Zhaoqing, Zhou Ming-Dong

机构信息

School of Chemistry and Materials Science , Liaoning Shihua University , Fushun 113001 , P. R. China.

Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Science , Lanzhou University , Lanzhou 730000 , P. R. China.

出版信息

Org Lett. 2020 Feb 21;22(4):1542-1546. doi: 10.1021/acs.orglett.0c00134. Epub 2020 Jan 28.

Abstract

In this study, a facile and efficient method to synthesize monofluoroalkenes by photoredox catalytic defluorinative alkylation of -difluoroalkenes with 4-alkyl-1,4-dihydropyridines under mild conditions (room temperature) is described. This novel strategy is applicable for a broad range of -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.

摘要

本研究描述了一种简便高效的方法,即在温和条件(室温)下,通过光氧化还原催化的二氟烯烃与4-烷基-1,4-二氢吡啶的脱氟烷基化反应来合成单氟烯烃。这种新策略适用于多种具有良好官能团耐受性的二氟烯烃底物以及各种4-烷基-1,4-二氢吡啶(包括伯、仲甚至叔烷基自由基)。此外,它还能实现与基于糖基的4-烷基-1,4-二氢吡啶(DHPs)进行具有挑战性的自由基偶联反应,以合成单氟烯基化糖类。

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