通过炔酮的无金属转移氢化和氰化反应，轻松获得三氟甲基丙炔醇。

IF 2.9 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2024-11-12 DOI:10.1039/d4ob00844h

Devadkar Ajitrao Kisan, Ishita Paul, Soumyadip Dey, Abhijit Sau, Tarun K Panda

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引用次数: 0

摘要

我们报告了一条在常温温和的反应条件下，使用频哪醇硼烷（4,4,5,5-四甲基-1,3,2-二氧杂硼烷）和三甲基硅基氰化物，对多种三氟甲基炔基酮体进行无金属氢硼化和氰硅化反应的高效合成路线。这些高效的氢硼化和氰硅化反应可在水解后生成相应的炔基三氟甲基丙炔醇。此外，还利用丙炔醇合成了基于三氟甲基（CF3）基团的具有药物活性的恩氟昔布类似物。

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Facile access to trifluoromethyl propargyl alcohol by metal-free transfer hydrogenation and cyanation of alkynyl ketones.

We report an efficient synthetic route to the metal-free hydroboration and cyanosilylation of a wide range of alkynyl trifluoromethyl ketones using pinacolborane (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) and trimethylsilyl cyanide under mild reaction conditions at ambient temperature. These highly effective hydroboration and cyanosilylation reactions lead to the corresponding alkynyl trifluoromethyl propargyl alcohols after hydrolysis. In addition, trifluoromethyl (CF₃) group-based pharmaceutically active enflicoxib analogs were synthesized from propargyl alcohol.

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来源期刊

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： The international home of synthetic, physical and biomolecular organic chemistry.