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Intramolecular Homolytic Aromatic Substitution of Alkyl 2-Benzimidazolyl Sulfones as a Means of Entry into Alkyl Radicals for Organic Synthesis.作为有机合成中引入烷基自由基的一种方法:2-苯并咪唑基砜的分子内均裂芳香取代反应
Tetrahedron Lett. 2008 Apr 28;49(18):2999-3003. doi: 10.1016/j.tetlet.2008.02.174.
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本文引用的文献

1
Is there a homolytic substitution chemistry (SH2) of sulfones?砜类是否存在均裂取代化学(SH2)?
J Org Chem. 2005 Sep 16;70(19):7672-8. doi: 10.1021/jo050990c.
2
CYCLIZED SUBSTITUTED THIOUREAS. III. 1-SUBSTITUTED-TETRAZOLINES-5-THIONES.环化取代硫脲。III. 1-取代-四唑啉-5-硫酮
J Pharm Sci. 1963 Sep;52:909-10. doi: 10.1002/jps.2600520923.
3
Intramolecular aromatic 1,5-hydrogen transfer in free radical reactions III. Reactivity of diaryl ketones, ethers, thioethers, sulfoxydes, and sulfones. An experimental and theoretical study.自由基反应中的分子内芳香族1,5-氢转移III. 二芳基酮、醚、硫醚、亚砜和砜的反应活性。一项实验与理论研究。
Org Lett. 2003 Apr 17;5(8):1175-8. doi: 10.1021/ol027301t.

作为有机合成中引入烷基自由基的一种方法:2-苯并咪唑基砜的分子内均裂芳香取代反应

Intramolecular Homolytic Aromatic Substitution of Alkyl 2-Benzimidazolyl Sulfones as a Means of Entry into Alkyl Radicals for Organic Synthesis.

作者信息

Crich David, Grant Daniel

机构信息

Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Il 60607-7061.

出版信息

Tetrahedron Lett. 2008 Apr 28;49(18):2999-3003. doi: 10.1016/j.tetlet.2008.02.174.

DOI:10.1016/j.tetlet.2008.02.174
PMID:19404382
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2615488/
Abstract

The intramolecular radical aromatic substitution of heteroaryl sulfones by tethered aryl radicals has been investigated as a source of alkyl radicals. The 1-(2-iodobenzyl)benzimidazole-2-sulfonyl system was found to be the most effective, while a tetrazole-based system did not undergo the desired radical aromatic substitution at all. Application of the benzimidazole-based system to the generation of alkyl radical and their subsequent use in radical cyclizations was demonstrated.

摘要

通过连接的芳基自由基对杂芳基砜进行分子内自由基芳香取代反应已作为烷基自由基的一种来源进行了研究。发现1-(2-碘苄基)苯并咪唑-2-砜体系最为有效,而基于四唑的体系根本不发生所需的自由基芳香取代反应。展示了基于苯并咪唑的体系在生成烷基自由基及其随后用于自由基环化反应中的应用。