Recent advances on the synthetic applications of the dithioacetal functionality

C–S Bond Activation

“…Luh did a seminal work on cross-coupling of alkyl sulfides, specifically dithioacetals. The reaction of dithioacetals with alkylmagnesium reagents provided alkylidenated products instead of the expected dialkylated products (Scheme 11) [30,31]…”

Dithioacetals as Zwitterion Synthons

“…[19][20][21][22]36] The major limitation of this reaction is the use of Grignard reagents: substrates containing carbonyl or cyano groups, terminal alkynes, etc. As described in Scheme 1, dithioacetals can be olefinated through treatment with Grignard reagents in the presence of catalytic amounts of NiCl 2 (PPh 3 ) 2 .…”

“…As described in Scheme 1, dithioacetals can be olefinated through treatment with Grignard reagents in the presence of catalytic amounts of NiCl 2 (PPh 3 ) 2 . [19][20][21][22]36] The major limitation of this reaction is the use of Grignard reagents: substrates containing carbonyl or cyano groups, terminal alkynes, etc. cannot be used under the reaction conditions.…”

“…The most frequent usage of this functional group has been restricted to its serving as a latent carbonyl [16] or methylene group. [19][20][21][22][23] In these cases, the dithioacetal moiety can be regarded as a dication synthon or a carbene synthon (Scheme 1). Selective displacements of these two bonds by carbon-carbon bonds can be useful in organic synthesis.…”

“…Earlier works on the reactions involving conversion of the two carbon-sulfur bonds into carbon-carbon bonds have been reviewed. [19][20][21][22][23] In these cases, the dithioacetal moiety can be regarded as a dication synthon or a carbene synthon (Scheme 1). Scheme 1. The dithioacetal functionality can be viewed as a special kind of thioether.…”