α，β -不饱和亚胺与原位生成的二氟苯[4 + 1]环加成合成2 -氟吡咯

IF 2.7 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2025-09-26 DOI:10.1002/ejoc.202500586

Kohei Fuchibe , Takaya Miura , Junji Ichikawa

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引用次数: 0

摘要

2‐氟吡啶是通过α，β‐不饱和亚胺与二氟苯（:CF2）的[4 + 1]环加成合成的，二氟苯是由三甲基硅基2,2‐二氟‐2‐（氟磺酰）醋酸酯（TFDA）原位生成的。在质子海绵催化剂的存在下，用TFDA处理α，β‐不饱和亚胺，促进了：CF2的催化生成。通过亚甲酰亚胺中间体与亚胺进行[4 + 1]环加成，得到5,5‐二氟吡咯。随后用1,8 -重氮双环[5.4.0]- 7 -十一烯进行脱氢氟化反应，产生目标的2 -氟吡咯。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Synthesis of 2‐Fluoropyrroles via [4 + 1] Cycloaddition of α,β‐Unsaturated Imines with In Situ‐Generated Difluorocarbene

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Synthesis of 2‐Fluoropyrroles via [4 + 1] Cycloaddition of α,β‐Unsaturated Imines with In Situ‐Generated Difluorocarbene

2‐Fluoropyrroles are synthesized via the [4 + 1] cycloaddition of α,β‐unsaturated imines with difluorocarbene (:CF₂), which is generated in situ from trimethylsilyl 2,2‐difluoro‐2‐(fluorosulfonyl)acetate (TFDA). The α,β‐unsaturated imines are treated with TFDA in the presence of a Proton Sponge catalyst, facilitating the catalytic generation of: CF₂. The resulting carbene underwent [4 + 1] cycloaddition with imines through azomethine ylide intermediates, yielding 5,5‐difluoropyrrolines. Subsequent dehydrofluorination with 1,8‐diazabicyclo[5.4.0]‐7‐undecene produced the targeted 2‐fluoropyrroles.

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来源期刊

European Journal of Organic Chemistry 化学-有机化学

CiteScore

5.40

自引率

3.60%

发文量

752

审稿时长

1 months

期刊介绍： The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.