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Rhodium complexes with a new chiral nitrogen‐containing BINOL‐based diphosphite or phosphonite ligand: synthesis and application to hydroformylation of styrene and/or hydrogenation of prochiral olefins
Author(s) -
Kostas Ioannis D.,
Vallianatou Kalliopi A.,
Holz Jens,
Börner Armin
Publication year - 2005
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.977
Subject(s) - hydroformylation , chemistry , rhodium , styrene , ligand (biochemistry) , organic chemistry , catalysis , nitrogen , combinatorial chemistry , polymer chemistry , copolymer , receptor , biochemistry , polymer
Two new cationic rhodium(I) complexes with a chiral nitrogen‐containing BINOL‐based diphosphite or phosphonite ligand have been synthesized. Chiral diphosphite was prepared by the reaction of N ‐phenyldiethanolamine with two equivalents of [( R )‐(1,1′‐binaphthalene‐2,2′‐diyl)]chlorophosphite. In its rhodium complex the ligand is bound to the metal via both phosphorus atoms, and a Rh–N interaction is also possible. Synthesis of the chiral phosphonite was achieved by the reaction of 2‐( N , N ‐dimethylaminophenyl)‐bis(diethylamino)phosphine with one equivalent of R ‐BINOL. In its rhodium complex, the ligand is P , N ‐bonded, forming a five‐membered chelate ring. The first complex was applied to hydroformylation of styrene and displayed high activity and chemo‐ and regioselectivity, but unfortunately no asymmetric induction was found. Both complexes were evaluated in the hydrogenation of prochiral olefins with moderate activities and low enantioselectivities. Copyright © 2005 John Wiley & Sons, Ltd.