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Ferrocene‐Based Chiral Phosphine‐Triazines: A New Family of Highly Efficient P,N Ligands for Asymmetric Catalysis
Author(s) -
Hu XiangPing,
Chen HuiLin,
Zheng Zhuo
Publication year - 2005
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200404240
Subject(s) - chemistry , phosphine , ferrocene , allylic rearrangement , amination , tsuji–trost reaction , catalysis , moiety , triazine , reactivity (psychology) , ligand (biochemistry) , medicinal chemistry , enantioselective synthesis , combinatorial chemistry , stereochemistry , organic chemistry , electrochemistry , medicine , biochemistry , alternative medicine , receptor , pathology , electrode
Abstract The presence of the additional heterocyclic nitrogen atoms in chiral P,N ligands has an important influence on the asymmetric catalysis, and a clear trend was observed in the present research that the enantioselectivity and reactivity were significantly increased by raising the number of heterocyclic nitrogen atoms in these P,N ligands. Through finely tuning the number of heterocyclic nitrogen atoms, a new family of ferrocene‐based chiral phosphine‐triazine ligands with three heterocyclic nitrogen atoms has been developed and successfully applied in Pd‐catalyzed asymmetric allylic substitution. Up to 99% ee with 99% yield of allylic alkylation products and 94% ee of allylic amination products have been obtained by the use of ligand ( R c , S p )‐ 1f with a 4,6‐diphenoxy‐1,3,5‐triazine moiety.