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Synlett 2011(20): 3031-3035
DOI: 10.1055/s-0031-1289907
DOI: 10.1055/s-0031-1289907
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New YorkMetal-Free Relay Oxidation: Valuable Synthesis of Acylsilane and Ketones under Aerobic Oxidation
Further Information
Received
18 October 2011
Publication Date:
23 November 2011 (online)
Publication History
Publication Date:
23 November 2011 (online)
Abstract
In this letter, an example of interesting metal-free relay air oxidation of α-hydroxysilanes, promoted by the hydroperoxidated carbonyl compounds derived from the Michael reaction of 5,5-dimethylcyclohexane-1,3-dione and chalcone, is reported. A series of aromatic acylsilanes with TBDPS were obtained in promising isolated yields. In addition, as an extension of the relay oxidation under aerobic conditions, this catalyst-free relay oxidation induced by diketone can be applied to the oxidation of general aromatic alcohols (up to 75% yield).
Key words
catalyst-free - oxidation - silane - ketone - relay chemistry
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