ChemInform Abstract: Synthesis of Allyl Sulfoxides from Allylsilanes via Silyl Sulfinates

ChemInform 2015
Agnese Stikute, Vilnis Peipiņš, Māris Turks

Allylsilanes underwent sila-ene reaction with sulfur dioxide in the presence of Lewis acid catalysts. The obtained Vogel’s silyl sulfinates were found to act as sulfinyl transfer agents in reactions with aryl, heteroaryl, alkyl, and allyl Grignard reagents proceeding with the expulsion of the trialkylsilyloxy group to give allyl sulfoxides in up to 83% yield. The nucleophilic attack of Grignard reagents was accelerated in toluene and in the presence of LiCl or ZnCl2 as Lewis acidic additives. The developed method allows the transformation of allylsilanes into allyl sulfoxides.

Keywords
Sila-ene reaction; Sulfur dioxide; Silyl sulfinates; Trimethylsilyl 2-methylprop-2-ene-1-sulfinate; Sulfoxides; Grignard reagents
DOI
10.1002/chin.201545105
Hyperlink
http://onlinelibrary.wiley.com/doi/10.1002/chin.201545105/abstract

Stikute, A., Peipiņš, V., Turks, M. ChemInform Abstract: Synthesis of Allyl Sulfoxides from Allylsilanes via Silyl Sulfinates. ChemInform, 2015, Vol.46, Iss.45, pp.1-2. ISSN 0931-7597. e-ISSN 1522-2667. Available from: doi:10.1002/chin.201545105

Publication language
English (en)