One-Pot Synthesis of Alkyl Styryl Sulfides Free from Transition Metal/Ligand Catalyst and Thiols

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One-Pot Synthesis of Alkyl Styryl Sulfides Free from Transition Metal/Ligand Catalyst and Thiols

http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201201163/abstract

European Journal of Organic Chemistry

Early View (Online Version of Record published before inclusion in an issue)

Adrián A. Heredia and Alicia B. Peñéñory
Article first published online: 19 DEC 2012 | DOI: 10.1002/ejoc.201201163

They have developed a one-pot methodology for the synthesis of alkyl arylvinyl sulfides in good to excellent yields, free of any metal/ligand systems and from malodorous and air-sensitive alkyl thiols. This procedure uses commercially available potassium thioacetate, low temperatures, and short reaction times.

abstract

A new protocol for the one-pot synthesis of styryl alkyl sulfides was developed. This methodology involves the in situ generation of thiolate anions by nucleophilic substitution between potassium thioacetate and alkyl halides followed by fragmentation. Further reactions of these thiolate anions with substituted (E,Z)-β-styryl halides gave the corresponding sulfides with retention of stereochemistry in good to excellent yields. This procedure does not require a metal catalyst, it proceeds under mild conditions and in short times, and it is free from malodorous and air-sensitive alkyl thiols.

 

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