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One‐Pot Synthesis of Alkyl Styryl Sulfides Free from Transition Metal/Ligand Catalyst and Thiols
Author(s) -
Heredia Adrián A.,
Peñéñory Alicia B.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201163
Subject(s) - chemistry , alkyl , halide , catalysis , nucleophile , transition metal , nucleophilic substitution , ligand (biochemistry) , metal , medicinal chemistry , organic chemistry , polymer chemistry , biochemistry , receptor
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.