%0 Journal Article %T Conditions for the Palladium-Catalysed Direct 2-Arylation of 3-Bromobenzo[b]thiophene Tolerant of the Benzothienyl Carbon-Bromine Bond %+ Institut des Sciences Chimiques de Rennes (ISCR) %+ Laboratoire de Synthèse Organique Asymétrique et Catalyse Homogène %A Smari, Imen %A Ben Ammar, Hamed %A Ben Hassine, Bechir %A Soulé, Jean-François %A Doucet, Henri %< avec comité de lecture %@ 0039-7881 %J Synthesis: Journal of Synthetic Organic Chemistry %I Georg Thieme Verlag %V 47 %N 21 %P 3354-3362 %8 2015 %D 2015 %R 10.1055/s-0034-1378733 %Z Chemical Sciences %Z Chemical Sciences/Material chemistryJournal articles %X Phosphine-free palladium(II) acetate catalyst was found to promote the direct 2-arylation of 3-bromobenzo[b]thiophene without cleavage of the benzothienyl carbon-bromine bond, allowing the synthesis of 2-aryl-3-bromobenzo[b]thiophenes in only one step. The best results were generally obtained using a low loading of the palladium catalyst (0.5 mol%), quite low reaction temps. (80-120 °C) and short reaction times (0.5-2 h). The reaction proceeds with electron-deficient para-, meta- and ortho-substituted aryl bromides and also with heteroaryl bromides. The benzothienyl carbon-bromine bond has been profitably employed for further palladium-catalyzed functionalisations. This strategy allows the straightforward synthesis of 2,3-di(hetero)arylated benzo[b]thiophenes with two different (hetero)aryl units via sequential catalytic arylations. %G English %2 https://univ-rennes.hal.science/hal-01188188/document %2 https://univ-rennes.hal.science/hal-01188188/file/Synthesis-Imen%20BromobenzothiophenesRev.pdf %L hal-01188188 %U https://univ-rennes.hal.science/hal-01188188 %~ UNIV-RENNES1 %~ CNRS %~ INSA-RENNES %~ ENSC-RENNES %~ ISCR %~ SCR_OMC2012 %~ ISCR-OMC %~ STATS-UR1 %~ UR1-SPM %~ INC-CNRS %~ UR1-UFR-SPM %~ UR1-HAL %~ UR1-SDLM %~ UR1-SDLMJONCH %~ TEST-UNIV-RENNES %~ TEST-UR-CSS %~ UNIV-RENNES %~ INSA-GROUPE %~ UR1-MMS %~ TEST2-HALCNRS