91548-08-2

Usage

Uses

Used in Organometallic Chemistry:
(6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diyl)bis(diphenylphosphine) is used as a ligand for organometallic complexes, where it coordinates with metal atoms to form stable complexes. Its ability to bind with metals enhances the stability and reactivity of these complexes, making it a crucial component in organometallic chemistry.
Used in Catalysis:
In the field of catalysis, (6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diyl)bis(diphenylphosphine) is employed as a ligand to create catalysts that can facilitate various chemical reactions. Its unique structure allows it to improve the efficiency and selectivity of catalytic processes, making it an important compound in industrial applications.
Used in Chemical Reactions:
(6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diyl)bis(diphenylphosphine) is used as a catalyst or a catalyst component in a range of chemical reactions, including cross-coupling reactions, hydrogenation, and olefin polymerization. Its presence in these reactions can lead to improved reaction rates, higher yields, and better control over product selectivity.
Used in Industrial Processes:
(6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diyl)bis(diphenylphosphine) (6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diyl)bis(diphenylphosphine) is utilized in various industrial processes, where its catalytic properties can be harnessed to improve the efficiency and sustainability of chemical production. Its applications in this context can lead to cost savings, reduced environmental impact, and the development of new materials and products.

Upstream product

• 3840-88-8 6,6'-dimethyl-2,2'-dibromo-1,1'-biphenyl 
• 1079-66-9 chloro-diphenylphosphine 

Downstream Products

• 126253-61-0 {Rh(nbd)(S)-(+)-BIPHEMP}ClO₄ 
• 91602-77-6 {(+)-(S)-(6,6'-dimethylbiphenyl-2,2'-diyl)bis(diphenylphosphine)}(η4-8,9,10-trinorborna-2,5-diene)-rhodium(I) tetrafluoroborate 
• 120521-80-4 (Rh{(S)-(6,6'-dimethylbiphenyl-2,2'-diyl)bis(diphenylphosphine)}{(Z,Z)-1,5-cyclooctadiene})BF₄ 
• 91514-12-4 (Rh{(S)-(6,6'-dimethylbiphenyl-2,2'-diyl)bis(diphenylphosphine)}{(Z,Z)-1,5-cyclooctadiene})ClO₄ 
• 1160606-21-2 ((S)-biphemp)Rh(CO)2(BF₄) 
• 91602-77-6 (-)-{Rh(nbd)(R)-(-)-BIPHEMP}BF₄ 
• 120521-80-4 (Rh{(R)-(6,6'-dimethylbiphenyl-2,2'-diyl)bis(diphenylphosphine)}{(Z,Z)-1,5-cyclooctadiene})BF₄ 
• 132434-22-1 (Rh{(R)-(6,6'-dimethylbiphenyl-2,2'-diyl)bis(diphenylphosphine)}{(Z,Z)-1,5-cyclooctadiene})ClO₄ 
• 140482-33-3 {2,2'-dimethyl-6,6'-bis(diphenylphosphino)biphenyl}(triphenylphosphine)dichlororuthenium(II) 

Relevant academic research and scientific papers

Process for producing optically active gamma-butyrolactone

This invention provides a novel process for producing optically active 3-hydroxy-γ-butyrolactone in a short step, which is superior economically and in efficiency and industrially suitable by using a starting material which is inexpensive and easily available and reagents easy to handle. This invention relates to a process for producing optically active 3-hydroxy-γ-butyrolactone represented by formula I: wherein the symbol * means an asymmetric carbon atom, which comprises hydrogenating an optically active 4-substituted oxy-3-hydroxybutyrate represented by formula II: wherein R1 represents a C1-4 lower alkyl group, R2 represents a protective group for a hydroxyl group deprotected by hydrogenation with a heterogeneous hydrogenation catalyst, and the symbol * has the same meaning as defined above, in the presence of a heterogeneous hydrogenation catalyst and an acidic substance followed by deprotection and simultaneous ring closure thereof.

Method for producing 1-menthol

Provided is a method for the production of 1-menthol, which comprises hydrogenation of piperitenone with a transition metal complex of a specified optically active phosphine to produce pulegone, hydrogenation of the obtained pulegone with a ruthenium-phosphine-amine complex in the presence of base to obtain pulegol, and further hydrogenation of the pulegol with a transition metal catalyst.

Asymmetrical hydrogenation

There is disclosed a process for the asymmetrical hydrogenation of (E)-2-methyl-3-phenyl-2-propen-1-ol of formula STR1 wherein R1 is as defined herein, to give compounds of formula STR2 The catalyst is a neutral or cationic rhodium complex of a chiral atropisomeric phosphine.

2,2'-Dimethyl-6,6'-bis(diphenylphosphino)biphenyl (BIPHEMP) as a Chiral Ligand for Transition Metal Catalyzed Asymmetric Synthesis of Binaphthyls and for Asymmetric Hydrogenation. A Comparison with BINAP

The chiral biphosphine ligand 1 has been prepared via optically active 2,2'-dilithio-6,6'-dimethyldiphenyl and used in the synthesis of optically active binaphthyls through palladium catalyzed c

Axially Dissymmetric Bis(triaryl)phosphines in the Biphenyl Series: Synthesis of (6,6'-Dimethylbiphenyl-2,2'-diyl)bis(diphenylphosphine) ('BIPHEMP') and Analogues, and their Use in Rh(I)-Catalyzed Asymmetric Isomerisations of N,N-Diethylnerylamine

The axially dissymmetric diphosphines (-)-(R)- and (+)-(S)-(6,6'-dimethylbiphenyl-2,2'-diyl)bis(diphenylphosphine)((-)-(R)-10 and (+)-(S)-10; 'BIPHEMP') have been synthesized, starting from (R)- and (S)-6,6'-dimethylbiphenyl-2,2'-diamine ((R)- and (S)-16), respectively, via Sandmeyer reaction, lithiation, and phosphinylation.Moreover, racemic 4,4'-dimethyl- and 4,4'-bis(dimethylamino)-substituted analogues 11 and 12, respsctively, and the 6,6'-bridged analogue 1,11-bis(diphenylphosphino)-5,7-dihydrodibenzoxepin (13) were synthesized and resolved into optically pure (R)- and (S)-enantiomers via complexation with di-μ-chlorobisphenyl-C,N>dipalladium(II) ((R)-18).The molecular structures of the diphosphines (S)-10 and (R)-13 and of two derived cationic Rh(I) complexes, BF4 and BF4 were determined by X-ray analyses.Absolute configurations were established for (+)-(S)-10 by X-ray analyses of both the free diphosphine and of the derived Rh(I) complex, and for (-)-13 by X-ray analysis of the derived Rh(I) complex.Configurational assignments for the substituted BIPHEMP analogues 11 and 12 were achieved by means of 1H-NMR comparisons of the Pd(II) complexes derived from the diphosphines and (R)-18, and by means of CD comparisons.The BIPHEMP ligand 10 and analogues 11, 12, and 13 are the first examples of optically active bis(triarylphosphines) containing the axially dissymmetric biphenyl moiety.All these new diphosphines proved to be excellent asymmetry-inducing ligands in Rh(I)-catalyzed isomerizations of N,N-diethylnerylamine affording citronellal enamine of 98-99percent ee.

Process for the manufacture of optically active compounds

The manufacture of optically active bifunctional compounds of the general formula STR1 wherein R represents protected hydroxymethyl, protected formyl or alkoxycarbonyl and R1 represents a group of the formula STR2 or --CH2 --CH=NR2 in which R2 and R3 represent lower alkyl or cycloalkyl or R2 and R3 together with the nitrogen atom represent a heterocyclic ring, by isomerizing compounds of the general formula STR3 wherein R, R2 and R3 have the above significance and R3 can additionally signify hydrogen, is described. The compounds of formula I are potential intermediates in the manufacture of, inter alia, natural vitamin E and natural vitamin K1.

Phosphorus compounds

Novel chiral phosphorus compounds of the general formula STR1 wherein R signifies substituted or unsubstituted phenyl, R1 and R2, which can be the same or different, signify hydrogen, lower alkyl, lower alkoxy, di-lower alkylamino or protected hydroxymethyl or R1 and R2 together signify the group STR2 in which m represents a number 3 to 5, R4 represents lower alkyl, substituted or unsubstituted phenyl or benzyl and R5 represents lower alkyl or both R5 's together represent lower alkylene, R3 signifies methyl, lower alkoxy, di-lower alkylamino or fluorine and n signifies the number 0, 1, 2 or 3, are described. The compounds of formula I are useful in the form of complexes with a metal of Group VIII as catalysts for asymmetric hydrogenations and enantioselective hydrogen displacements in prochiral allylic systems.