连续流可见光催化2h -氮嘧啶与烯酮的正(3 + 2)-环加成合成Δ1-Pyrrolines

IF 4.3 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

ACS Omega Pub Date : 2025-04-23 eCollection Date: 2025-05-06 DOI:10.1021/acsomega.5c01416

Lorena S R Martelli, Lucas G Furniel, Pedro H O Santiago, Javier Ellena, Arlene G Corrêa

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引用次数: 0

摘要

本文报道了在连续流动下，通过2H-azirines与烯酮的形式(3 + 2)-环加成，在可见光的促进下首次合成Δ1-pyrrolines。在30 min的停留时间内共制备了22个三取代Δ1-pyrrolines样品，产率为41-93%，非对映比高达7:3。此外，以查尔酮为起始原料的连续流动条件也是有效的，通过光催化环加成-氧化序列，生成了7个四取代吡咯，总收率在12%至47%之间。

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Synthesis of Δ¹-Pyrrolines via Formal (3 + 2)-Cycloaddition of 2H-Azirines with Enones Promoted by Visible Light under Continuous Flow.

This work reports the first synthesis of Δ¹-pyrrolines promoted by visible light under continuous flow, achieved through the formal (3 + 2)-cycloaddition of 2H-azirines to enones. A total of 22 examples of trisubstituted Δ¹-pyrrolines were prepared in only 30 min of residence time, with 41-93% yield and diastereomeric ratios up to 7:3. Furthermore, continuous flow conditions were also effective when chalcones were used as starting materials, leading to the formation of 7 tetrasubstituted pyrroles with an overall yield ranging from 12 to 47%, via a photocatalyzed cycloaddition-oxidation sequence.

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来源期刊

ACS Omega Chemical Engineering-General Chemical Engineering

CiteScore

6.60

自引率

4.90%

发文量

3945

审稿时长

2.4 months

期刊介绍： ACS Omega is an open-access global publication for scientific articles that describe new findings in chemistry and interfacing areas of science, without any perceived evaluation of immediate impact.