Hypervalent λ3-Bromane Strategy for Baeyer− Villiger Oxidation: Selective Transformation of Primary Aliphatic and Aromatic Aldehydes to Formates, Which is Missing …

…, A Yoshimura, K Miyamoto, S Hayashi…

Index: Ochiai, Masahito; Yoshimura, Akira; Miyamoto, Kazunori; Hayashi, Satoko; Nakanishi, Waro Journal of the American Chemical Society, 2010 , vol. 132, # 27 p. 9236 - 9239

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Citation Number: 21

Abstract

A conceptually distinct, modern strategy for Baeyer− Villiger oxidation (BVO) was developed. Our novel method involves initial hydration of water to carbonyl compounds, followed by ligand exchange of hypervalent aryl-λ3-bromane on bromane (III) with the resulting hydrate, yielding a new type of activated Criegee intermediate. The intermediate undergoes BV rearrangement and produces an ester via facile reductive elimination of an aryl-λ3- ...