Oxidation Catalysis by an Aerobically Generated Dess-Martin Periodinane Analogue.
Oxidation Catalysis by an Aerobically Generated Dess-Martin Periodinane Analogue.
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有氧产生的戴斯-马丁高碘烷类似物的氧化催化。
DOI：
10.1002/anie.201804159
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发表时间：
2018
影响因子：
--
通讯作者：
D. Powers
中科院分区：
文献类型：
--
作者：
A. Maity;Sung;Alan K. Wortman;D. Powers
高价碘（V）试剂，例如戴斯-马丁高碘烷（DMP）和2-碘酰苯甲酸（IBX），是化学合成中广泛有用的氧化剂。从分子氧（O2）产生这些试剂的策略的开发将立即使得能够在广泛的底物氧化反应中使用O2作为终端氧化剂。最近，我们公开了通过拦截醛自氧化过程中产生的反应性氧化剂来有氧合成I（III）试剂。在这项工作中，碘苯的有氧氧化与最初产生的I（III）化合物的反硝化反应相结合，以产生I（V）试剂。需氧生成的I（V）试剂表现出与B2 O3类似的底物氧化化学。I（V）的有氧产生使I（V）中间体在有氧氧化催化中的首次应用成为可能。
Hypervalent iodine(V) reagents, such as Dess-Martin periodinane (DMP) and 2-iodoxybenzoic acid (IBX), are broadly useful oxidants in chemical synthesis. Development of strategies to generate these reagents from dioxygen (O2 ) would immediately enable use of O2 as a terminal oxidant in a broad array of substrate oxidation reactions. Recently we disclosed the aerobic synthesis of I(III) reagents by intercepting reactive oxidants generated during aldehyde autoxidation. In this work, aerobic oxidation of iodobenzenes is coupled with disproportionation of the initially generated I(III) compounds to generate I(V) reagents. The aerobically generated I(V) reagents exhibit substrate oxidation chemistry analogous to that of DMP. The developed aerobic generation of I(V) has enabled the first application of I(V) intermediates in aerobic oxidation catalysis.