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烯烃无金属邻二胺化反应的最新进展:合成策略与机理洞察

Recent Advancements on Metal-Free Vicinal Diamination of Alkenes: Synthetic Strategies and Mechanistic Insights.

作者信息

Kumar Ravinder, Khanna Yugam, Kaushik Parul, Kamal Raj, Khokhar Shiwani

机构信息

Department of Chemistry, MMEC, Maharishi Markandeshwar (Deemed to be University), Mullana, Ambala, 133207, Haryana (INDIA.

Department of Chemistry, Kurukshetra University, Kurukshetra, 136119, Haryana, INDIA.

出版信息

Chem Asian J. 2023 Apr 17;18(8):e202300017. doi: 10.1002/asia.202300017. Epub 2023 Mar 21.

DOI:10.1002/asia.202300017
PMID:36869415
Abstract

The oxidative aminative vicinal difunctionalization of alkenes or related chemical feedstocks has emerged as sustainable and multipurpose strategies that can efficiently construct two -N bonds, and simultaneously prepare the synthetically fascinating molecules and catalysis in organic synthesis that typically required multi-step reactions. This review summarized the impressive breakthroughs on synthetic methodologies (2015-2022) documented especially over inter/intra-molecular vicinal diamination of alkenes with electron-rich or deficient diverse nitrogen sources. These unprecedented strategies predominantly involved iodine-based reagents/catalysts, which resent the interest of organic chemists due to their impressive role as flexible, non-toxic, and environmentally friendly reagents, resulting in a wide variety of synthetically useful organic molecules. Moreover, the information collected also describes the significant role of catalyst, terminal oxidant, substrate scope, synthetic applications, and their unsuccessful results to highlight the limitations. Special emphasis has been given to proposed mechanistic pathways to determine the key factors governing the issues of regioselectivity, enantioselectivity, and diastereoselectivity ratios.

摘要

烯烃或相关化学原料的氧化胺化邻位双官能团化已成为可持续且多功能的策略,可有效构建两个氮键,同时制备在有机合成中通常需要多步反应的具有合成吸引力的分子和催化剂。本综述总结了(2015 - 2022年)在合成方法学方面取得的显著突破,特别是关于烯烃与富电子或贫电子的各种氮源进行分子间/分子内邻位二胺化的研究。这些前所未有的策略主要涉及碘基试剂/催化剂,由于它们作为灵活、无毒且环境友好的试剂所发挥的重要作用,引起了有机化学家的兴趣,从而产生了各种各样具有合成价值的有机分子。此外,收集到的信息还描述了催化剂、终端氧化剂、底物范围、合成应用以及它们的不成功结果所起的重要作用,以突出局限性。特别强调了所提出的机理途径,以确定控制区域选择性、对映选择性和非对映选择性比率问题的关键因素。

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