Defluorinative Alkylation of Trifluoromethyl Alkenes with Soft Carbon Nucleophiles Enabled by a Catalytic Amount of Base was written by Gao, Ya;Qin, Wei;Tian, Ming-Qing;Zhao, Xuefei;Hu, Xu-Hong. And the article was included in Advanced Synthesis & Catalysis in 2022.Electric Literature of C10H20O This article mentions the following:
Direct manipulation of readily accessible trifluoromethyl alkenes (TAs) represents an attractive approach to the preparation of diversified fluorine-containing compounds In this study, defluorinative alkylation reactions of TAs with a broad array of soft carbon nucleophiles have been documented. Nucleophilic substitutions occur enabled by a catalytic amount of base, providing access to tertiary alkyl substituted gem-difluoroalkenes and 2-fluoro-4H-pyrans. By extending the nucleophiles to silyl enol ethers, defluorination can be achieved in the absence of base to give gem-difluoroalkenes. This process, which eliminates the requirement of organometallic reagents, transition metals, or strong bases for the C-F bond cleavage, is applicable to late-stage modification of complex mols. In the experiment, the researchers used many compounds, for example, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5Electric Literature of C10H20O).
(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Electric Literature of C10H20O
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts