Oxidation of N,N-Disubstituted Hydroxylamines to Nitrones with Hypervalent Iodine Reagents

被引：50
|
作者：
Matassini, Camilla [1 ]
Parmeggiani, Camilla [1 ,2 ,3 ]
Cardona, Francesca [1 ]
Goti, Andrea [1 ]
机构：
[1] Univ Florence, Dipartimento Chim Ugo Schiff Polo Sci & Tecnol, I-50019 Sesto Fiorentino, FI, Italy
[2] CNR, INO, I-50019 Sesto Fiorentino, FI, Italy
[3] LENS, I-50019 Sesto Fiorentino, FI, Italy
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 16期
关键词：
IODOXYBENZOIC ACID IBX; PYRROLINE N-OXIDES; ONE-POT SYNTHESIS; SECONDARY-AMINES; HYDROGEN-PEROXIDE; CATALYTIC-OXIDATION; NITRILE OXIDES; CYCLIC NITRONES; CYCLOADDITION; PYRROLIZIDINE;
D O I：
10.1021/acs.orglett.5b02029
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Hypervalent iodine compounds are viable reagents for the oxidation of N,N-disubstituted hydroxylamines to the corresponding nitrones, with IBX performing best. The procedure is very simple and user-friendly and affords the target compounds with high efficiency and regioselectivity, highlighting IBX as the reagent of choice for preparation of aldonitrones from nonsymmetric hydroxylamines. Evidence for a mechanism involving nitrogen to iodine coordination has been collected.
引用
收藏
页码：4082 / 4085
页数：4
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