利用n -氟苯磺酰亚胺(NFSI)作为双功能多米诺试剂的远程激活策略激活(RASE) π键迁移脱烷基C-N偶联

IF 4.7 1区 化学 Q1 CHEMISTRY, ORGANIC
Jiahao Gu, Zhenyang Wan, Yuhong Lu, Xiangmin Tian, Ziyue Zeng, Dailin Zhuang, Ziyuan Li
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引用次数: 0

摘要

在温和条件下,通过C(sp3)-H和C(sp2)-H裂解,实现了远程激活策略激活(RASE) π键迁移脱烷基C(sp3)-N和C(sp2)-N与2-烷氧基噻唑的偶联,分别生成n -苄基或n -苯基噻唑-2(3H)- 1。n-氟苯磺酰亚胺(NFSI)是一种重要的双功能多米诺骨牌试剂,它不仅产生以氮为中心的自由基,引发N-C或N-N自由基接力,提供亲电偶联伙伴,而且还提供关键的碳阳离子清除剂n-氢苯磺酰亚胺(NHSI),引发2-烷氧基噻唑的π键迁移脱烷基反应,提供亲核噻唑-2(3H)- 1偶联伙伴。在机理研究的基础上,提出了合理的机理。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Remote Activating Strategy Enabled (RASE) π-Bond Migratory Dealkylative C-N coupling Utilising N-Fluorobenzenesulfonimide (NFSI) as A Bifunctional Domino Reagent
Remote activating strategy enabled (RASE) π-bond migratory dealkylative C(sp3)-N and C(sp2)-N coupling with 2-alkoxylthiazole through C(sp3)-H and C(sp2)-H cleavage, giving N-benzyl or N-phenyl thiazol-2(3H)-one, respectively, are achieved under mild conditions. N-Fluorobenzenesulfonimide (NFSI) serves as a crucial bifunctional domino reagent which not only generates nitrogen-centred radical that initiates N-C or N-N radical relay, offering electrophile coupling partner, but also provides the key carbocation scavenger, N-hydrobenzenesulfonimide (NHSI), triggering π-bond migratory dealkylation of 2-alkoxylthiazole which offers nucleophilic thiazol-2(3H)-one coupling partner. Plausible mechanism has been proposed based on the results of mechanistic studies.
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来源期刊
Organic Chemistry Frontiers
Organic Chemistry Frontiers CHEMISTRY, ORGANIC-
CiteScore
7.90
自引率
11.10%
发文量
686
审稿时长
1 months
期刊介绍: Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
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