82822-45-5

Basic information

• Product Name: phenylphosphinobinaphthyl cyclooctadiene ruthenium perchl.
• Synonyms: phenylphosphinobinaphthyl cyclooctadiene ruthenium perchl.
• CAS NO: 82822-45-5
• Molecular Formula: C₅₂H₄₄P₂Rh*ClO₄
• Molecular Weight: 931.21
• Mol File: 82822-45-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: phenylphosphinobinaphthyl cyclooctadiene ruthenium perchl.(CAS DataBase Reference)
• NIST Chemistry Reference: phenylphosphinobinaphthyl cyclooctadiene ruthenium perchl.(82822-45-5)
• EPA Substance Registry System: phenylphosphinobinaphthyl cyclooctadiene ruthenium perchl.(82822-45-5)

Safety Data

• RIDADR: 1479
• HazardClass: 5.1
• PackingGroup: III
• Hazardous Substances Data: 82822-45-5(Hazardous Substances Data)

Upstream product

• 12092-47-6 di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium 
• 76144-87-1 (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) 
• 76189-55-4 (R)-(+)-2,2’-bis(diphenylphosphino)-1,1’-binaphthalene 

Relevant articles and documents

DIPHOSPHINE LIGAND AND TRANSITION METAL COMPLEX USING THE SAME

The present invention provides a novel ligand represented by the following formula and a novel transition metal complex having the ligand, which shows superior enantioselectivity and catalytic efficiency, particularly high catalyst activity, in various asymmetric synthesis reactions. A transition metal complex having, as a ligand, a compound represented by the formula wherein R4 is a hydrogen atom or a C1-6 alkyl group optionally having substituent(s), and R5 and R6 are each a C1-6 alkyl group optionally having substituent(s), or the formula is a group represented by the formula wherein ring B is a 3- to 8-membered ring optionally having substituent (s).

HIGHLY ENANTIOSELECTIVE ISOMERIZATION OF PROCHIRAL ALLYLAMINES CATALYZED BY CHIRAL DIPHOSPHINE RHODIUM(I) COMPLEXES. PREPARATION OF OPTICALLY ACTIVE ENAMINES

Rh(I) complexes of types ClO4 and n>ClO4 (diphosphine = cis-chelating tertiary diphosphine; diene = 1,5-cyclooctadiene or norbornadiene; S = solvent) were found to be effective catalists for allylic hydrogen migration of tertiary and secondary allylamines to give the corresponding (E)-enamines and imines, respectively.Studies on diphosphine ligands with respect to the catalytic activity and product selectivity led to the discovery of a fully aryl-substituted diphosphine, BINAP , which produces very active Rh(I) complex catalysts.With ClO4 (COD = 1,5-cyclooctadiene) or n>ClO4 as catalyst, (Z)-(diethylnerylamine, 1) or (E)-N,N-diethyl-3,7-dimethyl-2,6-octadienylamine (diethylgeranylamine, 2) was isomerized into the racemic (E)-enamine (E)-N,N-diethyl-3,7dimethyl-1,6-octadienylamine (citronellenamine, 3) with a chemical selectivity of over 95percent, the 6-double bond being retained intact.A variety of substituted allylamines serves as the substrate, e.g., (E)-N,N-dimethyl-2-butenylamine, N,N-dimethyl-2-methyl-2-propenylamine, N,N-dimethyl-3-methyl-2-butenylamine, N,N-dimethyl-3-phenyl-2-butenylamine.Asymmetric isomerization of prochiral allylamines producing optically active enamines or imines can be effected with cationic Rh(I) complexes of various chiral diphosphine ligands such as (2R,3R)-DIOP and others.The ligand that gives the highest optical yield was (+)- or (-)-BINAP.Virtually perfect enantioselectivity (95-99percent ee) was achieved with + for the isomerization of 1 or 2 into the optically active (E)-enamine (3).A clear stereochemical correlation was established between the olefin geometry (E or Z) of substrates, the configuration of the chiral diphosphines (R or S), and the chiral carbon configuration of the product enamines (R or S).The present catalytic system thus provides a convenient and practical access to optically active aldehydes.For example, optically pure natural citronellal can be produced either from nerylamine with the Rh(I)-(+)-BINAP catalyst or from geranylamine with the Rh(I)-(-)-BINAP complex catalyst.