Synthesis of thiophene derivatives via palladium-catalyzed coupling reactions

Abstract

Thiophene derivatives with multiple substitutions are prepared from vinylidene bromide, which is synthesized by the reaction of thiophene-2-carboxaldehyde with carbon tetrabromide in the presence of PPh 3 , as a core molecule through several coupling reactions such as Suzuki-Miyaura coupling and palladium-catalyzed CH arylation. The reactions with a wide variety of organic halides lead to a series of substituted thiophene derivatives in moderate to good yields.

Microwave‐Assisted Dibromoolefination of Aromatic and Heteroaromatic Aldehydes and Ketones

“…Microwave reactions were run on a CEM Discover SP or Biotage Initiator Classic, each monomode apparatus. All known compounds (Table , entries 1 , 2 , 3 , 5 , 6 , 7 , and 11 ) afforded analytical data identical to those reported in literature (refer to Supporting Information for further details).…”

Palladium-acetate catalyst for regioselective direct arylation at C2 of 3-furanyl or 3-thiophenyl acrylates with inhibition of Heck type reaction

“…This is certainly due to the possible competitive Heck reaction with such substrates. [8][9][10][11] Heck reactions with benzalacetone, cinnamates or chalcone, proceed nicely. [12][13][14] Moreover, an example of Heck type reaction of 3-thiophen-3-ylacrylamide with iodobenzene has been described by Park and co-workers (Scheme 1, top).…”

Coupling Reactions Promoted by Silver

“…82 With organic thin-film transistors, light-emitting devices, and dye-sensitized organic solar cells as the ultimate targets; the same group more recently reported a synthesis of poly(arylated)thiophenes through a series of coupling reactions and a Pd-Ag-promoted arylation (Scheme 10.51). 83 Applications of this reaction are not limited to advanced materials, but can be applied to natural product synthesis. Indeed, indoles have quite recently (in 2008) been arylated in the presence of palladium acetate and silver oxide (Scheme 10.52).…”