Palladium-catalyzed intramolecular redox-relay Heck cyclization: access to heterocycles bearing all-carbon quaternary centers

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-05-19 DOI:10.1039/d5qo00431d

Linjun Qi, Rongjing He, Xiaofeng Tong, Shuling Yu

引用次数: 0

Abstract

While the intramolecular Heck reaction of aryl/vinyl halides with various alkenes has been well studied, the exploration of acyclic alkenol systems via a redox-relay strategy remains unexploited. Herein, we disclose the first palladium-catalyzed intramolecular redox-relay Heck cyclization of vinyl/aryl iodides with alkenols for establishing heterocyclic all-carbon quaternary centers. Diverse 5–7-membered (benzo)heterocycles with a remote carbonyl functionality are obtained in good to excellent yields using a bipyridine ligand. Moreover, an asymmetric version of this transformation could be realized in good yield with promising enantioselectivity.

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钯催化的分子内氧化还原-接力Heck环化：获得含全碳四元中心的杂环

虽然芳基/乙烯基卤化物与各种烯烃的分子内Heck反应已经得到了很好的研究，但通过氧化还原-接力策略探索无环烯醇体系仍未得到开发。在此，我们首次公开了钯催化的乙烯基/芳基碘化物与烯醇的分子内氧化还原-接力Heck环反应，以建立杂环全碳季中心。使用联吡啶配体可以获得具有远羰基官能团的各种5 - 7元（苯并）杂环，收率很高。此外，该转化的不对称版本可以实现良好的产率和有希望的对映体选择性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.