Journal
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
Volume 71, Issue 4, Pages 341-354Publisher
SOC SYNTHETIC ORGANIC CHEM JPN
DOI: 10.5059/yukigoseikyokaishi.71.341
Keywords
Pummerer reaction; sulfoxide; kene dithioacetal monoxide; trifluoromethyl group; furan; pyrrole; thiophene; copper catalyst; rearrangement; migration
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Ketene dithioacetal monoxides (KDMs) bring out a variety of latent intriguing reactivity upon treatment with triflic anhydride. The extended Pummerer reactions of KDMs provide reliable accesses to heteroaromatic compounds including (benzo) furan, (benzo) thiophene, and pyrroles. Trifluoromethyl-substituted KDMs are useful building blocks to prepare alpha-trifluoromethyl carbonyl compounds and 3-trifluoromethyl heteroaromatic compounds. A newly uncovered interrupted Pummerer reaction/ [3,3] sigmatropic rearrangement cascade is the key that realizes most of the transformations in this paper. The last part of this paper describes the first example of metal-catalyzed Pummerer reaction where sulfoxides are directly activated by the catalyst.
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