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基于醚类的饱和杂环的官能化反应,同时伴有需氧的C-H活化和C-C键形成。

Functionalisation of ethereal-based saturated heterocycles with concomitant aerobic C-H activation and C-C bond formation.

作者信息

Ahmed Nehaal, Spears Richard J, Sheppard Tom D, Chudasama Vijay

机构信息

Department of Chemistry, University College London 20 Gordon Street London WC1H 0AJ UK

出版信息

Chem Sci. 2022 Jun 27;13(29):8626-8633. doi: 10.1039/d2sc01626e. eCollection 2022 Jul 29.

DOI:10.1039/d2sc01626e
PMID:35974756
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9337743/
Abstract

With an ever-growing emphasis on sustainable synthesis, aerobic C-H activation (the use of oxygen in air to activate C-H bonds) represents a highly attractive conduit for the development of novel synthetic methodologies. Herein, we report the air mediated functionalisation of various saturated heterocycles and ethers aerobically generated radical intermediates to form new C-C bonds using acetylenic and vinyl triflones as radical acceptors. This enables access to a variety of acetylenic and vinyl substituted saturated heterocycles that are rich in synthetic value. Mechanistic studies and control reactions support an aerobic radical-based C-H activation mechanism.

摘要

随着对可持续合成的日益重视,需氧C-H活化(利用空气中的氧气活化C-H键)是开发新型合成方法的极具吸引力的途径。在此,我们报道了各种饱和杂环和醚通过需氧产生的自由基中间体进行空气介导的官能化反应,以乙炔基三氟甲磺酸酯和乙烯基三氟甲磺酸酯作为自由基受体形成新的C-C键。这使得能够获得各种具有丰富合成价值的乙炔基和乙烯基取代的饱和杂环。机理研究和对照反应支持基于需氧自由基的C-H活化机制。

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ChemSusChem. 2022 Feb 18;15(4):e202102441. doi: 10.1002/cssc.202102441. Epub 2022 Jan 31.
3
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European J Org Chem. 2021 Aug 6;2021(29):4038-4048. doi: 10.1002/ejoc.202100323. Epub 2021 May 5.
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5
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Angew Chem Int Ed Engl. 2021 Jan 11;60(2):946-953. doi: 10.1002/anie.202010846. Epub 2020 Nov 3.
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8
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