A new reagent for direct difluoromethylation.

A new reagent for direct difluoromethylation.
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DOI:
10.1021/ja211422g
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发表时间:
2012-01-25
影响因子:
15
通讯作者:
Baran, Phil S.
Baran, Phil S.
中科院分区:
化学1区
文献类型:
--
作者:
Fujiwara, Yuta;Dixon, Janice A.;Rodriguez, Rodrigo A.;Baxter, Ryan D.;Dixon, Darryl D.;Collins, Michael R.;Blackmond, Donna G.;Baran, Phil S.

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含有烷基氟取代基的分子支架在从材料到药物的许多化学研究领域都是需要的。在此,我们报告了一种新的试剂(Zn(SO2CF2H)2, DFMS)的发明,用于有机底物通过自由基过程的先天二氟甲基化。这种温和,操作简单,化学选择性和可扩展的二氟甲基化方法是兼容的一系列含氮杂芳烃底物的不同复杂性,以及选择类共轭π系统和硫醇。区域化学比较表明,新试剂生成的CF2H自由基具有亲核性质。
Molecular scaffolds containing alkylfluorine substituents are desired in many areas of chemical research from materials to pharmaceuticals. Herein, we report the invention of a new reagent (Zn(SO2CF2H)2, DFMS) for the innate difluoromethylation of organic substrates via a radical process. This mild, operationally simple, chemoselective, and scalable difluoromethylation method is compatible with a range of nitrogen-containing heteroarene substrates of varying complexity as well as select classes of conjugated π-systems and thiols. Regiochemical comparisons suggest that the CF2H radical generated from the new reagent possesses nucleophilic character.
固有的和引导的 C-H 功能化逻辑。
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