Oxidation of Alkenes with H2O2 by an in-Situ Prepared Mn(II)/Pyridine-2-carboxylic Acid Catalyst and the Role of Ketones in Activating H2O2

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• 作者：Jia Jia Dong ; Pattama Saisaha ; Tim G. Meinds ; Paul L. Alsters ; Edwin G. Ijpeij ; Ruben P. van Summeren ; Bin Mao ; Mart铆n Fa帽an谩s-Mastral ; Johannes W. de Boer ; Ronald Hage ; Ben L. Feringa ; Wesley R. Browne
• 刊名：ACS Catalysis
• 出版年：2012
• 出版时间：June 1, 2012
• 年：2012
• 卷：2
• 期：6
• 页码：1087-1096
• 全文大小：555K
• 年卷期：v.2,no.6(June 1, 2012)
• ISSN：2155-5435

文摘

A simple, high yielding catalytic method for the multigram scale selective epoxidation of electron-rich alkenes using near-stoichiometric H₂O₂ under ambient conditions is reported. The system consists of a Mn(II) salt (<0.01 mol %), pyridine-2-carboxylic acid (<0.5 mol %), and substoichiometric butanedione. High TON (up to 300鈥?00) and TOF (up to 40 s^鈥?) can be achieved for a wide range of substrates with good to excellent selectivity, remarkable functional group tolerance, and a wide solvent scope. It is shown that the formation of 3-hydroperoxy-3-hydroxybutan-2-one from butanedione, and H₂O₂ in situ, is central to the activity observed.

Keywords:

manganese; epoxidation; cis-dihydroxylation; hydrogen peroxide