2008
DOI: 10.1016/j.tetlet.2007.12.010
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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.

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Cited by 45 publications
(17 citation statements)
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“…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).…”
Section: Methodssupporting
confidence: 63%
“…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).…”
Section: Methodssupporting
confidence: 63%
“…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).…”
Section: Introductionmentioning
confidence: 94%
“…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).…”
Section: Silver In Pd II -Promoted Electrophilic Substitution Of Arenmentioning
confidence: 99%