A Phosphonium Ylide as an Ionic Nucleophilic Catalyst for Primary Hydroxyl Group Selective Acylation of Diols

Carbonyl-stabilized phosphonium ylides exhibit great utility in modern organic synthesis, and they are known as an ambident nucleophile at the carbonyl oxygen atom and at the α-carbon atom. However, they have found limited use as catalysts. We focused on the inherent nucleophilicity of the oxygen at...

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Bibliographic Details
Published in:ACS catalysis 2017-09, Vol.7 (9), p.6150-6154
Main Authors: Toda, Yasunori, Sakamoto, Tomoyuki, Komiyama, Yutaka, Kikuchi, Ayaka, Suga, Hiroyuki
Format: Article
Language:English
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Summary:Carbonyl-stabilized phosphonium ylides exhibit great utility in modern organic synthesis, and they are known as an ambident nucleophile at the carbonyl oxygen atom and at the α-carbon atom. However, they have found limited use as catalysts. We focused on the inherent nucleophilicity of the oxygen atom to develop an ionic nucleophilic catalysis, and the phosphonium ylide-catalyzed primary alcohol selective acylation of mixed diols with acid anhydrides has been demonstrated. Mechanistic studies revealed the behavior of a catalyst, which would contribute to the field of ylide chemistry.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.7b02281