Synthesis of Trifluoromethylated Alkenes via a Tandem Aldol/<i>N</i>-Acyloxyphthalimide-Assisted Decarboxylation Sequence

We have developed a metal-free approach for synthesizing <i>E</i>-trifluoromethylated alkenes from readily available aldehydes and the <i>N</i>-hydroxyphtalimide ester of trifluoropropionic acid. To address the challenge of defluorination, we conducted high-throughput screening of reaction conditions. We discovered that acid-base co-catalysis effectively suppresses defluorination, thereby enhancing product yields. A key advantage of our method is its reliance on inexpensive, commercially available starting materials and straightforward reaction conditions.

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Publication Details

Journal
Organic Letters
Published
2025-04-09
DOI
https://doi.org/10.1021/acs.orglett.5c00601
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Synthesis of Trifluoromethylated Alkenes via a Tandem Aldol/N-Acyloxyphthalimide-Assisted Decarboxylation Sequence

Fei Huang, Bo Xu, Yunquan Man
Organic Letters
Fluorine in Organic Chemistry
article

Synthesis of Trifluoromethylated Alkenes via a Tandem Aldol/N-Acyloxyphthalimide-Assisted Decarboxylation Sequence

Fei Huang, Bo Xu, Yunquan Man
article en

Abstract

We have developed a metal-free approach for synthesizing <i>E</i>-trifluoromethylated alkenes from readily available aldehydes and the <i>N</i>-hydroxyphtalimide ester of trifluoropropionic acid. To address the challenge of defluorination, we conducted high-throughput screening of reaction conditions. We discovered that acid-base co-catalysis effectively suppresses defluorination, thereby enhancing product yields. A key advantage of our method is its reliance on inexpensive, commercially available starting materials and straightforward reaction conditions.

Organic LettersVol. 27(15)
Donghua University (CN), Wanhua Chemical (China) (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 95%
Fluorine in Organic Chemistry
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