Copper-Catalyzed Synthesis of Difluoromethyl Alkynes from Terminal and Silyl Acetylenes
Copper-Catalyzed Synthesis of Difluoromethyl Alkynes from Terminal and Silyl Acetylenes
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DOI：
10.1021/acs.joc.2c02799
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发表时间：
2023-01-09
影响因子：
3.6
通讯作者：
Prakash，G. K. Surya
中科院分区：
文献类型：
--
作者：
Ispizua-Rodriguez，Xanath;Krishnamurti，Vinayak;Prakash，G. K. Surya
本发明公开了一种用于末端炔的直接C（sp）-H二氟甲基化和（三甲基甲硅烷基）乙炔的脱甲硅烷基-二氟甲基化的有效方法。铜催化的转化提供了获得各种各样的结构不同的CF2 H炔在良好的产率，利用（二氟甲基）锌试剂和有机氧化剂。展示了重要的二氟甲基化反应物和API。这些（二氟甲基）炔的合成效用通过选择的环加成反应来证明。此外，对反应条件的轻微修改允许选择性地制备2-二氟甲基吲哚。
An efficient method for the direct C(sp)–H difluoromethylation of terminal alkynes and the desilylation–difluoromethylation of (trimethylsilyl)acetylenes is disclosed. The copper-catalyzed transformation provides access to a wide range of structurally diverse CF2H alkynes in good yields, utilizing a (difluoromethyl)zinc reagent and an organic oxidant. The difluoromethylation of important synthons and API’s is showcased. The synthetic utility of these (difluoromethyl)alkynes is demonstrated by selected cycloaddition reactions. Additionally, a slight modification to the reaction conditions allowed the selective preparation of a 2-difluoromethylindole.