Redox-Neutral Coupling of Allyl Alcohols with Trifluoromethyl Ketones via Synergistic Ni–Ti Bimetallic Catalysis

A redox-neutral coupling of allyl alcohols with trifluoromethyl ketones has been developed via Ni-Ti bimetallic catalysis. This innovative method allows for the efficient synthesis of various β-tertiary trifluoromethyl alcohol-substituted ketones with yields of up to 98%. The reaction is scalable and compatible with a wide range of substrates, including complex bioactive molecules. Mechanistic studies suggest that the rate-determining step involving β-H elimination and the presence of the Ti-based Lewis acid, as well as a hydroxyl group on the substrates, is crucial for driving the reactivity of this transformation.

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Publication Details

Journal
Organic Letters
Published
2024-08-26
DOI
https://doi.org/10.1021/acs.orglett.4c02720
Citations
8
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
2.00

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article

Redox-Neutral Coupling of Allyl Alcohols with Trifluoromethyl Ketones via Synergistic Ni–Ti Bimetallic Catalysis

Yong Li, Lei Tang, Jiang‐Fei Li, Jiayu Huang et al.
8 citations
Organic Letters
Catalytic C–H Functionalization Methods
2.00
article

Redox-Neutral Coupling of Allyl Alcohols with Trifluoromethyl Ketones via Synergistic Ni–Ti Bimetallic Catalysis

Yong Li, Lei Tang, Jiang‐Fei Li, Jiayu Huang, Xiangkai Kong, Rong‐Hua Wang, Jianta Wang, Bo Li, Bin Liu, Jiquan Zhang, Siyu He, Ming-Bai Gou, Zhen-Qi Luo, Qing He
article en
8 citations

Abstract

A redox-neutral coupling of allyl alcohols with trifluoromethyl ketones has been developed via Ni-Ti bimetallic catalysis. This innovative method allows for the efficient synthesis of various β-tertiary trifluoromethyl alcohol-substituted ketones with yields of up to 98%. The reaction is scalable and compatible with a wide range of substrates, including complex bioactive molecules. Mechanistic studies suggest that the rate-determining step involving β-H elimination and the presence of the Ti-based Lewis acid, as well as a hydroxyl group on the substrates, is crucial for driving the reactivity of this transformation.

Organic LettersVol. 26(35)
Wannan Medical College (CN), Guiyang Medical University (CN)
Health Commission of Guizhou Province, National Natural Science Foundation of China, Guizhou Medical University, Science and Technology Program of Guizhou Province
Clean water and sanitation
Openalex Percentile: Top 14%
Catalytic C–H Functionalization Methods
2.00
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