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光氧化还原自由基/极性交叉反应实现了烯烃的碳-杂官能化:便捷合成1,3-二官能化硝基化合物。

Photoredox radical/polar crossover enables carbo-heterofunctionalization of alkenes: facile access to 1,3-difunctionalized nitro compounds.

作者信息

Patra Subrata, Valsamidou Vasiliki, Nandasana Bhargav N, Katayev Dmitry

机构信息

Department of Chemistry, Biochemistry and Pharmaceutical Sciences, University of Bern, Freiestrasse 3, 3012 Bern, Switzerland.

出版信息

Chem Commun (Camb). 2025 Jan 21;61(8):1689-1692. doi: 10.1039/d4cc06005a.

DOI:10.1039/d4cc06005a
PMID:39749586
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11696862/
Abstract

Herein, we present an efficient and practical method for multicomponent carbo-heterofunctionalization of alkenes radical-polar crossover photoredox catalysis. Employing geminal bromonitroalkanes as redox-active reagents with a wide range of O-centered nucleophiles allows rapid access to various 1,3-difunctionalized nitro compounds, including β-nitro ketones, 1,3-nitro alcohols, 1,3-nitro ethers as well as cyclic molecules.

摘要

在此,我们展示了一种用于烯烃多组分碳-杂官能化的高效实用方法——自由基-极性交叉光氧化还原催化。使用偕二溴硝基烷烃作为氧化还原活性试剂与多种以氧为中心的亲核试剂,能够快速获得各种1,3-二官能化硝基化合物,包括β-硝基酮、1,3-硝基醇、1,3-硝基醚以及环状分子。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/99bc/11696862/e8602edf8e60/d4cc06005a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/99bc/11696862/116c0d9c2a5d/d4cc06005a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/99bc/11696862/fe61be3f9d9a/d4cc06005a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/99bc/11696862/c2cce4fb3f6b/d4cc06005a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/99bc/11696862/14e6e72502ba/d4cc06005a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/99bc/11696862/e8602edf8e60/d4cc06005a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/99bc/11696862/116c0d9c2a5d/d4cc06005a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/99bc/11696862/fe61be3f9d9a/d4cc06005a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/99bc/11696862/c2cce4fb3f6b/d4cc06005a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/99bc/11696862/14e6e72502ba/d4cc06005a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/99bc/11696862/e8602edf8e60/d4cc06005a-s5.jpg

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Mechanochemistry Drives Alkene Difunctionalization via Radical Ligand Transfer and Electron Catalysis.
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