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Palladium‐Catalyzed Three‐Component Cascade Cyclization Reaction of Bisallenes with Propargylic Carbonates and Organoboronic Acids: Efficient Construction of cis ‐Fused Bicyclo[4.3.0]nonenes
Author(s) -
Shu Wei,
Jia Guochen,
Ma Shengming
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.200805422
Subject(s) - palladium , bicyclic molecule , catalysis , chemistry , cascade , combinatorial chemistry , component (thermodynamics) , medicinal chemistry , stereochemistry , organic chemistry , physics , chromatography , thermodynamics
A bicycle built for two : The title reaction affords cis ‐fused bicyclo[4.3.0]nonenes from readily available 1,5‐bisallenes with structurally diverse propargylic carbonates and arylboronic acids (see scheme; X=NTs, C(E 1 ) 2 with E 1 =CO 2 Bn, SO 2 Ph, dba= trans , trans ‐dibenzylidenacetone). The reaction may involve a sequential oxidative addition, two different types of three carbopalladations, and a Suzuki‐type coupling.