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光氧化还原与镍催化合并实现的位点选择性远程sp C-H羧基化反应

Site-Selective, Remote sp C-H Carboxylation Enabled by the Merger of Photoredox and Nickel Catalysis.

作者信息

Sahoo Basudev, Bellotti Peter, Juliá-Hernández Francisco, Meng Qing-Yuan, Crespi Stefano, König Burkhard, Martin Ruben

机构信息

Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.

Institut für Organische Chemie, Universität Regensburg, Universitätstrasse 31, 93053, Regensburg, Germany.

出版信息

Chemistry. 2019 Jul 5;25(38):9001-9005. doi: 10.1002/chem.201902095. Epub 2019 Jun 6.

DOI:10.1002/chem.201902095
PMID:31074058
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6773098/
Abstract

A photoinduced carboxylation of alkyl halides with CO at remote sp C-H sites enabled by the merger of photoredox and Ni catalysis is described. This protocol features a predictable reactivity and site selectivity that can be modulated by the ligand backbone. Preliminary studies reinforce a rationale based on a dynamic displacement of the catalyst throughout the alkyl side chain.

摘要

本文描述了通过光氧化还原和镍催化的结合实现的在远程sp C-H位点上卤代烃与CO的光诱导羧基化反应。该方法具有可预测的反应性和位点选择性，可通过配体骨架进行调节。初步研究强化了基于催化剂在整个烷基侧链上动态位移的原理。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e3f/6773098/99afd9dc92d0/CHEM-25-9001-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e3f/6773098/e34bc69ece15/CHEM-25-9001-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e3f/6773098/dd12201f9fc8/CHEM-25-9001-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e3f/6773098/936bb8618f0d/CHEM-25-9001-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e3f/6773098/b343c1f7b674/CHEM-25-9001-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e3f/6773098/99afd9dc92d0/CHEM-25-9001-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e3f/6773098/e34bc69ece15/CHEM-25-9001-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e3f/6773098/dd12201f9fc8/CHEM-25-9001-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e3f/6773098/936bb8618f0d/CHEM-25-9001-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e3f/6773098/b343c1f7b674/CHEM-25-9001-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9e3f/6773098/99afd9dc92d0/CHEM-25-9001-g005.jpg

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本文引用的文献

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Elucidation of a Redox-Mediated Reaction Cycle for Nickel-Catalyzed Cross Coupling.阐明镍催化交叉偶联反应的氧化还原介导反应循环。
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NiH-Catalyzed Remote Asymmetric Hydroalkylation of Alkenes with Racemic α-Bromo Amides.
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J Am Chem Soc. 2024 Jan 24;146(3):1753-1759. doi: 10.1021/jacs.3c11205. Epub 2024 Jan 9.
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Native Amides as Enabling Vehicles for Forging spsp Architectures via Interrupted Deaminative Ni-Catalyzed Chain-Walking.通过间断脱氨酶 Ni 催化的链行走反应构建 spsp 结构的助化酰胺。
J Am Chem Soc. 2023 Feb 22;145(7):3869-3874. doi: 10.1021/jacs.2c12915. Epub 2023 Feb 8.
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Suppressing carboxylate nucleophilicity with inorganic salts enables selective electrocarboxylation without sacrificial anodes.用无机盐抑制羧酸盐亲核性可实现无牺牲阳极的选择性电羧化反应。
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