Nickel-Catalyzed Olefination of Unactivated Aliphatic Dithioacetals

Abstract

[reaction: see text] Olefination of aliphatic dithioacetals with Grignard reagents is catalyzed by Ni(acac)(2) in the presence of an appropriate trialkylphosphine ligand.

Dithioacetal as a 1,1-zwitterion synthon. Synthesis of functionalized alkenes by the coupling of benzylic dithioacetals with another 1,1-zwitterion synthon

“…1 The reaction can also proceed with aliphatic substrates when trialkylphosphine ligands are employed. 2 The major limitation of this olefination reaction is the use of Grignard reagents. Substrates containing functional groups such as carbonyl, cyano groups, terminal alkynes, etc., cannot be employed under the reaction conditions.…”

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.…”

Dithioacetals as Zwitterion Synthons

“…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.…”