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高价碘试剂的最新进展:烯烃、炔烃和杂环的无金属官能化。

Updates on hypervalent-iodine reagents: metal-free functionalisation of alkenes, alkynes and heterocycles.

机构信息

Department of Chemistry, Indian Institute of Technology Guwahati, 781039, Assam, India.

出版信息

Org Biomol Chem. 2022 Mar 9;20(10):2005-2027. doi: 10.1039/d1ob02233d.

Abstract

Hypervalent iodine (HVI) chemistry is a rapidly growing subdomain of contemporary organic chemistry because of its enormous synthetic applications. The high nucleofugality of the phenyliodonio group (-IPh) and its radical nature, serving as a single-electron oxidant makes HVI compounds highly valuable in organic synthesis. Due to the feasibility and benignity, reactions that rely solely on HVI reagents as promoters have received particular interest. Considering their great influence and synthetic potential, we contribute a brief synopsis on this field with a specific emphasis on metal-free functionalisations of alkenes, alkynes and heterocycles. The discussion is divided according to the type of substrate and reaction type and elaborated with mechanism and representative examples.

摘要

高价碘(HVI)化学是当代有机化学中一个迅速发展的分支领域,因为它具有巨大的合成应用。苯碘鎓基团(-IPh)的高亲核性和自由基性质使其成为单电子氧化剂,使得 HVI 化合物在有机合成中非常有价值。由于其可行性和良性,仅依靠 HVI 试剂作为促进剂的反应引起了特别的关注。考虑到它们的巨大影响和合成潜力,我们对这一领域进行了简要概述,特别强调了烯烃、炔烃和杂环的无金属官能化。讨论根据底物和反应类型进行划分,并通过机理和代表性实例进行了详细阐述。

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