Copper-Catalyzed Oxidation of Hydrazones to Diazo Compounds Using Oxygen as the Terminal Oxidant

Wenbin  Liu; Jack  Twilton; Bo  Wei; Maizie  Lee; Melissa N.  Hopkins; John  Bacsa; Shannon S.  Stahl; Huw M. L.  Davies

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Copper-Catalyzed Oxidation of Hydrazones to Diazo Compounds Using Oxygen as the Terminal Oxidant

机译：使用氧气作为末端氧化剂的铜催化的腙氧化到重氮化合物

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A mild method for accessing diazo compounds via aerobic oxidation of hydrazones is described. This catalytic transformation employs a Cu(OAc)_(2)/pyridine catalyst and molecular oxygen from ambient air as the terminal oxidant, generating water as the sole byproduct and affording the desired diazo compounds within minutes at room temperature. A broad array of electronically diverse aryldiazo esters, ketones, and amides can be accessed. Pyridine dramatically enhances the rate of the reaction by solubilizing the copper catalyst and serving as the Br?nsted base in the turnover-limiting proton-coupled oxidation of hydrazone by copper(II). Insights gained from mechanistic studies led to expansion of the scope of this method to include diaryl hydrazones, delivering diaryl diazomethane derivatives, which cannot be accessed via established diazo transfer methods. The products of this method may be employed in rhodium carbene catalysis without isolation of the diazo intermediate to afford cyclopropane products in good yield with high enantioselectivity.

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来源
《ACS catalysis》 |2021年第5期|共8页
作者
Wenbin Liu; Jack Twilton; Bo Wei; Maizie Lee; Melissa N. Hopkins; John Bacsa; Shannon S. Stahl; Huw M. L. Davies;
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作者单位

Department of Chemistry Emory University;

Department of Chemistry University of Wisconsin-Madison;

Department of Chemistry Emory University;

Department of Chemistry Emory University;

Department of Chemistry University of Wisconsin-Madison;

Department of Chemistry Emory University;

Department of Chemistry University of Wisconsin-Madison;

Department of Chemistry Emory University;

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正文语种 eng
中图分类物理化学（理论化学）、化学物理学;
关键词
copper; aerobic oxidation; dehydrogenation; hydrazones; diazo compounds; mechanism;

机译：铜;有氧氧化;脱氢;腙;双佐化合物;机制;

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Copper-Catalyzed Oxidation of Hydrazones to Diazo Compounds Using Oxygen as the Terminal Oxidant

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