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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 46, 2016 - Issue 7
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Original Articles

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

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Pages 636-644 | Received 30 Dec 2015, Published online: 11 Mar 2016
 

ABSTRACT

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.

GRAPHICAL ABSTRACT

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