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光催化和钴催化的不饱和胍、(异)脲及碳酸酯的环异构化反应

Photo- and Cobalt-Catalyzed Cycloisomerization of Unsaturated Guanidines, (Iso-)Ureas, and Carbonates.

作者信息

Lindner Henry, Carreira Erick M

机构信息

Laboratory of Organic Chemistry, Department of Chemistry and Applied Biosciences, ETH Zürich, 8093 Zurich, Switzerland.

出版信息

Org Lett. 2025 Jan 17;27(2):704-708. doi: 10.1021/acs.orglett.4c04695. Epub 2025 Jan 8.

DOI:10.1021/acs.orglett.4c04695
PMID:39772755
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11744792/
Abstract

We report intramolecular photocatalyzed cycloisomerization of unactivated olefins with pendant nucleophiles. The reaction proceeds under mild conditions and utilizes guanidines, ureas, isoureas, isothioureas, and carbonates to yield several different five-, six-, and seven-membered heterocycles. Use of benzothiazinoquinoxaline as an organophotocatalyst and cobalt-salen catalyst obviates the need for a stoichiometric oxidant or reductant.

摘要

我们报道了未活化烯烃与侧链亲核试剂的分子内光催化环异构化反应。该反应在温和条件下进行,利用胍、脲、异脲、异硫脲和碳酸盐生成几种不同的五元、六元和七元杂环。使用苯并噻嗪并喹喔啉作为有机光催化剂和钴-萨伦催化剂避免了对化学计量的氧化剂或还原剂的需求。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7b30/11744792/4e048c03a5a2/ol4c04695_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7b30/11744792/9374f04a980c/ol4c04695_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7b30/11744792/d3e3a6feb4d5/ol4c04695_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7b30/11744792/772c8861e141/ol4c04695_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7b30/11744792/4e048c03a5a2/ol4c04695_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7b30/11744792/9374f04a980c/ol4c04695_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7b30/11744792/d3e3a6feb4d5/ol4c04695_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7b30/11744792/772c8861e141/ol4c04695_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7b30/11744792/4e048c03a5a2/ol4c04695_0004.jpg

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本文引用的文献

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Angew Chem Int Ed Engl. 2024 Oct 24;63(44):e202409388. doi: 10.1002/anie.202409388. Epub 2024 Sep 24.
2
Synthesis of Primary Amines via Hydrogen Atom Transfer-Initiated Cyclization/Reduction Cascade of Unsaturated Nitriles.通过不饱和腈的氢原子转移引发的环化/还原级联合成伯胺。
Org Lett. 2024 Jul 5;26(26):5467-5471. doi: 10.1021/acs.orglett.4c01739. Epub 2024 Jun 24.
3
Cobalt-Catalyzed Photo-Semipinacol Rearrangement of Unactivated Allylic Alcohols.
钴催化未活化烯丙醇的光半频哪醇重排反应
Angew Chem Int Ed Engl. 2024 Aug 26;63(35):e202407827. doi: 10.1002/anie.202407827. Epub 2024 Jul 25.
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Photo- and Cobalt-Catalyzed Synthesis of Heterocycles via Cycloisomerization of Unactivated Olefins.通过未活化烯烃的环异构化实现光催化和钴催化的杂环合成。
Angew Chem Int Ed Engl. 2024 May 6;63(19):e202319515. doi: 10.1002/anie.202319515. Epub 2024 Mar 22.
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Co-Catalyzed Hydrofluorination of Alkenes: Photocatalytic Method Development and Electroanalytical Mechanistic Investigation.烯烃的共催化氢氟化反应:光催化方法开发与电分析机理研究
J Am Chem Soc. 2024 Feb 21;146(7):4380-4392. doi: 10.1021/jacs.3c10989. Epub 2024 Feb 1.
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A Dual Cobalt and Photoredox Catalysis for Hydrohalogenation of Alkenes.用于烯烃氢卤化反应的双钴与光氧化还原催化作用
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