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Efficient Synthesis of Benzothiophenes by an Unusual Palladium‐Catalyzed Vinylic CS Coupling
Author(s) -
Bryan Christopher S.,
Braunger Julia A.,
Lautens Mark
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200902843
Subject(s) - sonogashira coupling , alkene , catalysis , palladium , aryl , alkyne , chemistry , reagent , combinatorial chemistry , medicinal chemistry , alkyl , organic chemistry
The simultaneous construction of a CS and a CC bond under catalytic conditions forms the basis of an efficient route to diversely functionalized benzothiophenes from gem ‐dihalovinyl thiophenols. The CC bond can be formed in this tandem catalytic process with an organoboron reagent as shown in the scheme (R 1 =H, Me, F, Cl, Br, OCH 2 O; R 2 =H, Me; R 3 =aryl, heteroaryl, alkenyl, alkyl), or by Heck or Sonogashira coupling with an alkene or alkyne.