%0 Journal Article %T One Pot Access to 2'‐Aryl‐2,3'‐Bithiophenes via Twofold Palladium‐Catalyzed C‐X/C‐H Coupling Associated to a Pd‐1,4‐Migration %+ Institut des Sciences Chimiques de Rennes (ISCR) %A Liu, Linhao %A Doucet, Henri %< avec comité de lecture %@ 1615-4150 %J Advanced Synthesis and Catalysis %I Wiley-VCH Verlag %V 364 %N 16 %P 2783-2795 %8 2022-06-30 %D 2022 %R 10.1002/adsc.202200563 %Z Chemical SciencesJournal articles %X The reactivity of 1,2-dihalobenzenes in palladium catalyzed polyheteroarylation via C-H bond functionalization was investigated. The first catalytic cycle using thiophene as the heteroarene gives the expected 2-(2-bromophenyl)thiophenes. In the course of the second catalytic cycle, in the presence of heteroarenes having a free C3-position, a partial Pd 1,4-migration occurred giving rise to aryl-substituted biheteroarenes such as 2'-aryl-2,3'-bithiophenes as well as the expected 1,2-di(thiophen-2-yl)benzenes. The best selectivities in favor of the formation of 2'-aryl-2,3'-bithiophenes were obtained with electron-rich 1,2-dihalobenzenes. A wide variety of thiophene derivatives bearing useful functions such as formyl, acetyl, cyclopropylmethanone, 2-methyl-1,3-dioxolane, ester, nitrile or chloro was tolerated allowing to prepare poly-functionalized 2'-aryl-2,3'-bithiophenes. Moreover, this one pot preparation of 2'-aryl-2,3'-bithiophenes employs a low loading of an air stable commercially available palladium source associated to an inexpensive base. %G English %2 https://univ-rennes.hal.science/hal-03735527/document %2 https://univ-rennes.hal.science/hal-03735527/file/ASC%20Linhao%201%2C4-migration%20Hal.pdf %L hal-03735527 %U https://univ-rennes.hal.science/hal-03735527 %~ 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 %~ TEST-UR-CSS %~ UNIV-RENNES %~ INSA-GROUPE %~ UR1-MMS %~ TEST2-HALCNRS