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通过原子转移自由基加成(ATRA)途径实现碳-碳多重键的光诱导1,2-碳卤官能化反应。

Photo-induced 1,2-carbohalofunctionalization of C-C multiple bonds via ATRA pathway.

作者信息

Bag Debojyoti, Kour Harpreet, Sawant Sanghapal D

机构信息

Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Jammu, Canal Road, Jammu, Jammu & Kashmir 180001, India.

出版信息

Org Biomol Chem. 2020 Nov 7;18(41):8278-8293. doi: 10.1039/d0ob01454k. Epub 2020 Oct 2.

Abstract

Radical vicinal carbohalofunctionalization of C-C multiple bonds via atom transfer processes constitutes an efficient method for the construction of halogenated building blocks with complete atom economy via radical cleavage of a pre-existing carbon-halogen σ-bond of an atom transfer reagent and their transposition over the π-bond of alkenes and alkynes. This review summarizes the recent advances in the photo-induced version of this class of transformations. A variety of transition-metal complexes, organic dyes, phosphines, amines, phenols and aldehydes were utilized as catalysts for the cleavage of the existing carbon-halogen bond of the corresponding atom transfer reagent in the presence of a light source. Alongside a variety of 1,2-haloalkylation and haloperfluoroalkylation reactions, atom transfer radical addition (ATRA) or cyclization (ATRC) reactions via the cleavage of the carbon-halogen bonds of aryl halides are also discussed.

摘要

通过原子转移过程实现的C-C多重键的自由基邻位碳卤官能化,是一种通过原子转移试剂中预先存在的碳-卤σ键的自由基裂解及其在烯烃和炔烃的π键上的转位,以完全原子经济性构建卤化结构单元的有效方法。本综述总结了这类转化光诱导版本的最新进展。在光源存在下,多种过渡金属配合物、有机染料、膦、胺、酚和醛被用作催化剂,用于裂解相应原子转移试剂中现有的碳-卤键。除了各种1,2-卤烷基化和卤全氟烷基化反应外,还讨论了通过芳基卤化物的碳-卤键裂解进行原子转移自由基加成(ATRA)或环化(ATRC)反应。

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