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使用叔丁基过氧化氢(TBHP)的配体调控钯催化苯乙烯瓦克氧化反应的发现及其机理洞察

Discovery of and mechanistic insight into a ligand-modulated palladium-catalyzed Wacker oxidation of styrenes using TBHP.

作者信息

Cornell Candace N, Sigman Matthew S

机构信息

Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112-8500, USA.

出版信息

J Am Chem Soc. 2005 Mar 9;127(9):2796-7. doi: 10.1021/ja043203m.

Abstract

We describe the discovery of a new N-heterocyclic carbene-modulated Pd catalyst for the Wacker oxidation that does not require molecular oxygen but instead uses TBHP as a reagent in this oxidation. The catalyst activity and selectivity for the oxidation of styrene derivatives to methyl ketones are among the best reported. Preliminary mechanistic studies of the catalytic system were performed and show that the origin of the carbonyl oxygen is TBHP and that the hydrogens in the product all originate from the starting olefin.

摘要

我们描述了一种用于瓦克氧化反应的新型氮杂环卡宾调节的钯催化剂的发现,该催化剂不需要分子氧,而是使用叔丁基过氧化氢(TBHP)作为该氧化反应中的试剂。对于将苯乙烯衍生物氧化为甲基酮,该催化剂的活性和选择性是已报道的最佳结果之一。我们对该催化体系进行了初步的机理研究,结果表明羰基氧来源于叔丁基过氧化氢,且产物中的氢均来源于起始烯烃。

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