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首页> 外文期刊>ACS catalysis >Dual Photoredox/Nickel-Catalyzed Conversion of Aryl Halides to Aryl Aminooxetanes: Computational Evidence for a Substrate-Dependent Switch in Mechanism
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Dual Photoredox/Nickel-Catalyzed Conversion of Aryl Halides to Aryl Aminooxetanes: Computational Evidence for a Substrate-Dependent Switch in Mechanism

机译：双摄影毒剂/镍催化的芳基卤化物转化为芳基氨基肟：基板依赖性开关的计算证据

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摘要

A mild and direct strategy for the construction of aryl aminooxetanes has been accomplished through the synergistic combination of photoredox and nickel catalysis. This approach represents a rare example of harnessing challenging tertiary radicals in photoredox/nickel cross-coupling. Oxetanes are often employed in medicinal chemistry as carbonyl or gem-dimethyl bioisosteres, but their accessibility is hampered by the lack of practical synthetic methods. The strategy reported here utilizes a readily available oxetanyl amino acid building block in a cross-coupling manifold to rapidly access oxetane scaffolds with broad functional group tolerance. Computational studies reveal that a catalytic cycle beginning with Ni(0)-Ni(II) oxidative addition, rather than radical addition to Ni(0), is operative for reactions with aminooxetanyl radicals. Consequently, for radical-based photoredox/nickel-catalyzed cross-couplings, the preferred mechanistic pathway has a fundamental dependence on the identity of the radical.
机译：通过光致毒剂和镍催化的协同组合实现了一种温和的芳基氨基氧基氧基氨基氧丙烷的策略。这种方法代表了在光致毒剂/镍交叉耦合中利用挑战性三级基团的罕见例子。奥雪替斯经常用于药用化学作为羰基或宝石 - 二甲基生物蛋白剂，但通过缺乏实用的合成方法，它们的可用性受到阻碍。此处报告的策略利用交叉耦合歧管中的易于可用的奥替己基氨基酸构建块，以快速进入具有宽官能团耐受性的氧杂丁支架。计算研究表明，从Ni（0）-NI（II）氧化添加的催化循环，而不是Ni（0）的根本加入，用于与氨基氧基基团的反应。因此，对于基于自由基的光致毒剂/镍催化的交叉偶联，优选的机械途径对自由基的身份具有基本的依赖性。

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