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Synthesis and Characterization of Conformationally Rigid Chiral Pyridine–N‐Heterocyclic Carbene‐Based Palladacycles with an Unexpected Pd–N Bond Cleavage
Author(s) -
Ng Kim Hong,
Li Yongxin,
Tan Wei Xian,
Chiang Minyi,
Pullarkat Sumod A.
Publication year - 2013
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22116
Subject(s) - chemistry , carbene , racemization , pyridine , chirality (physics) , asymmetric carbon , axial chirality , stereochemistry , cleavage (geology) , enantioselective synthesis , stereocenter , bond cleavage , chiral resolution , catalysis , medicinal chemistry , organic chemistry , optically active , enantiomer , nambu–jona lasinio model , chiral symmetry breaking , physics , geotechnical engineering , quantum mechanics , fracture (geology) , engineering , quark
The versatility of a previously developed method for the synthesis of chiral carbene‐based palladacycles is demonstrated through the synthesis of two new chiral pyridine‐functionalized N‐heterocyclic carbene palladacycles with different wingtip groups. The efficiency in their resolution with different counter anions and different chiral amino acid salt auxiliaries has been studied. The absolute stereochemistries of all the chiral compounds were confirmed by single crystal X‐ray crystallography. An unexpected Pd–N bond cleavage that resulted in the racemization of the α‐carbon center in these complexes has also been investigated. Chirality 25:149–159, 2013 . © 2013 Wiley Periodicals, Inc.