Mechanisms of Activating Agents to Form Organozinc Reagents from Zinc Metal: Lessons for Reaction Design

IF 3.3 2区 化学 Q1 CHEMISTRY, ORGANIC
Martin Stang, Erin M. Hanada, Suzanne A. Blum
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引用次数: 0

Abstract

Activating agents enable the efficient preparation of organozinc complexes from zinc metal and organohalides, but their mechanisms had been obscured by the heterogeneous nature of these systems. Fluorescence microscopy, with the sensitivity to detect surface reaction intermediates, reveals distinct activating mechanisms of widely used activation strategies: trimethylsilyl chloride, LiCl, DMSO, and Rieke zinc powder. The resulting development of mechanistic models provides a better understanding of the oxidative-addition–solubilization sequence in organozinc reagent formation and contains lessons for methods development.

Abstract Image

活化剂从锌金属生成有机锌试剂的机理:对反应设计的启示
活化剂可以有效地从金属锌和有机卤化物中制备有机锌配合物,但由于这些体系的非均相性质,其作用机制一直模糊不清。荧光显微镜具有检测表面反应中间体的灵敏度,揭示了广泛使用的激活策略的不同激活机制:三甲基硅氯、LiCl、DMSO和Rieke锌粉。由此建立的机理模型提供了对有机锌试剂形成过程中氧化-加成-增溶顺序的更好理解,并为方法的发展提供了经验教训。
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来源期刊
Journal of Organic Chemistry
Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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