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Highly Enantiomerically Enriched Planar Chiral Naphthalene Tricarbonylchromium Complexes
Author(s) -
Cumming Graham R.,
Bernardinelli Gérald,
Kündig E. Peter
Publication year - 2006
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200600106
Subject(s) - chemistry , electrophile , aryl , chlorobenzene , naphthalene , enantiomer , halide , enantioselective synthesis , medicinal chemistry , quenching (fluorescence) , chromium , catalysis , organic chemistry , alkyl , physics , quantum mechanics , fluorescence
Lithiation/electrophile trapping reactions were carried out with the highly enantiomerically enriched complex [Cr(5‐bromonaphthalene)(CO) 3 ]. Electrophile quenching with ClPPh 2 , PhCHO, and (Me 3 SiO) 2 afforded the enantiomerically enriched (>97 % ee ) planar chiral 5‐substituted naphthalene complexes with PPh 2 , CH(Ph)OH, and OH substituents, respectively. Very mild Pd‐catalyzed Suzuki–Miyaura cross‐coupling reactions were developed and applied to the highly labile [Cr(5‐bromonaphthalene)(CO) 3 ] to give nine new planar chiral aryl‐, heteroaryl‐, alkynyl‐, and alkenylnaphthalene chromium complexes with high enantiomeric purity. The efficient ambient‐temperature coupling reactions with borinates prepared in situ were also applied to a number of chlorobenzene complexes and to aryl and vinyl halides.