Environmentally friendly procedure for the aqueous oxidation of benzyl alcohols to aldehydes with dibromodimethylhydantoin (DBDMH) and cyclodextrin: Scope and mechanistic insights

被引：10

作者：

Chaudhuri, Sauradip ^{[1
]}

Zaki, Hossam ^{[1
]}

Levine, Mindy ^{[1
]}

机构：

[1] Univ Rhode Isl, Dept Chem, 51 Lower Coll Rd, Kingston, RI 02881 USA

来源：

SYNTHETIC COMMUNICATIONS | 2016年 / 46卷 / 07期

基金：

美国国家科学基金会;

关键词：

Cyclodextrins; dibromodimethylhydantoin; hydrophobic effect; oxidation; supramolecular chemistry; BETA-CYCLODEXTRIN; N-BROMOSUCCINIMIDE; HYDANTOIN ENANTIOMERS; LIQUID-CHROMATOGRAPHY; NATURAL BENZALDEHYDE; WATER; CINNAMALDEHYDE; COMPLEXES; CHEMISTRY;

D O I：

10.1080/00397911.2016.1161801

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reported herein is an environmentally friendly procedure for the oxidation of benzyl alcohols to aldehydes using an inexpensive, commercially available reagent, 1,3-dibromo-5,5-dimethylhydantoin (DBDMH), and a variety of cyclodextrin additives under fully aqueous solvent conditions. This reaction proceeds with moderate to good yields for a broad scope of benzyl alcohol substrates, with the cyclodextrin acting to enhance the desired reactivity and limit undesired aromatic bromination side products. The reported experiments provide substantial mechanistic insight that will drive further reaction optimization and have broad-reaching applications.

引用

页码：636 / 644

页数：9

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