Efficient synthesis of 3-arylbutadiene sulfones using the Heck–Matsuda reaction
An efficient and practical method for a scalable synthesis of 3-arylbutadiene sulfones deals with the ligand-free Heck–Matsuda reaction of sulfolene with aryldiazonium tetrafluoroborates followed by triethylamine-promoted double bond shift.
4-Bromo-2-sulfolene and 4-bromo-3-methyl-2-sulfolene react with alkylcuprates to give direct substitution products, with vinyl- or phenylcuprates or sulfur-containing nucleophiles to give allylic substitution products, and with strongly basic nucleophiles to give elimination products.The allylic substitution products and the isomerized direct substitution products are precursors for substituted 1,3-butadienes.Thus, these 4-bromo-2-sulfolenes serve as butadienyl cation equivalents.
Chou, Ta-shue,Hung, Su Chun,Tso, Hsi-Hwa
p. 3394 - 3399
(2007/10/02)
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