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Synlett 2011(20): 3031-3035  
DOI: 10.1055/s-0031-1289907
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Metal-Free Relay Oxidation: Valuable Synthesis of Acylsilane and Ketones under Aerobic Oxidation

Xing-Feng Baia, Guang Gaoa, Zhan-Jiang Zhenga, Fei Lia, Guo-Qiao Laia, Kezhi Jianga, Fuwei Lib, Li-Wen Xu*a,b
a Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 310012, P. R. of China
Fax: +86(571)28865135; e-Mail: liwenxu@hznu.edu.cn; e-Mail: licpxulw@yahoo.com;
b State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China
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Publication History

Received 18 October 2011
Publication Date:
23 November 2011 (online)

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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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