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New Rigid Polycyclic Bis(phosphane) for Asymmetric Catalysis.


ABSTRACT: A simple, highly efficient synthesis of a series of novel chiral non-racemic rigid tetracyclic phosphorus ligands, applicable in important chemical asymmetric transformations, was performed. In a tandem cross-coupling/C-H bond activation reaction, a well-recognised and readily available ligand (R,R)-NORPHOS was used as the starting material. The palladium complexes of new ligands were obtained and characterised on the example of a crystalline dichloropalladium complex of [(1R,2R,9S,10S,11R,12R)-4-phenyltetracyclo[8.2.1.02,9.03,8]trideca-3,5,7-triene-11,12-diyl]bis(diphenylphosphane). A notably high activity and stereoselectivity of the palladium catalysts based on the new ligands were confirmed in a model asymmetric allylic substitution reaction. Herein, we discuss the geometry of the palladium complexes formed and its impact on the efficiency of the catalysts. A comparison of their geometric features with other bis(phosphane) ligand complexes found in the Cambridge Structural Database and built density functional theory (DFT) commutated models is also presented and rationalised.

SUBMITTER: Pietrusiewicz KM 

PROVIDER: S-EPMC6385021 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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New Rigid Polycyclic Bis(phosphane) for Asymmetric Catalysis.

Pietrusiewicz K Michał KM   Szwaczko Katarzyna K   Mirosław Barbara B   Dybała Izabela I   Jasiński Radomir R   Demchuk Oleg M OM  

Molecules (Basel, Switzerland) 20190205 3


A simple, highly efficient synthesis of a series of novel chiral non-racemic rigid tetracyclic phosphorus ligands, applicable in important chemical asymmetric transformations, was performed. In a tandem cross-coupling/C-H bond activation reaction, a well-recognised and readily available ligand <i>(R,R)-</i>NORPHOS was used as the starting material. The palladium complexes of new ligands were obtained and characterised on the example of a crystalline dichloropalladium complex of [(1<i>R</i>,2<i>R  ...[more]

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