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镍催化的二氟烯烃与硫代磺酸盐或硒代磺酸盐的脱氟还原交叉偶联反应

Nickel-Catalyzed Defluorinative Reductive Cross-Coupling Reaction of Difluoroalkenes with Thiosulfonate or Selenium Sulfonate.

作者信息

Li Jian, Rao Weidong, Wang Shun-Yi, Ji Shun-Jun

机构信息

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, and Collaborative Innovation Center of Suzhou Nano Science and Technology , Soochow University , Suzhou 215123 , China.

Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering , Nanjing Forestry University , Nanjing 210037 , China.

出版信息

J Org Chem. 2019 Sep 20;84(18):11542-11552. doi: 10.1021/acs.joc.9b01387. Epub 2019 Aug 28.

DOI:10.1021/acs.joc.9b01387
PMID:31424934
Abstract

A nickel-catalyzed defluorinative reductive cross-coupling of -difluoroalkenes with thiosulfonate or selenosulfonates is described. The reaction involves the formation of thiolated or selenylated monofluoroolefins via regioselective C-F bond cleavage and C-S or C-Se bond formation and features easily available substrates, mild reaction conditions, and high -selectivity. One of the derivatives by further cross coupling with PhMgBr exhibited an aggregation-induced emission enhancement effect.

摘要

本文描述了一种镍催化的二氟烯烃与硫代磺酸盐或硒代磺酸盐的脱氟还原交叉偶联反应。该反应通过区域选择性的C-F键裂解和C-S或C-Se键形成,生成硫醇化或硒醇化的单氟烯烃,具有底物易得、反应条件温和及高选择性的特点。其中一种衍生物与苯基溴化镁进一步交叉偶联后表现出聚集诱导发光增强效应。

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