CAS 199684-47-4 [NH2Me2][(RuCl((R)-binap))2(μ-Cl)3]

Synonyms

J-012887; (R)-[(RuCl(BINAP))2( -Cl)3][NH2Me2]; DIMETHYLAMMONIUM DICHLOROTRI(MU-CHLORO)BIS[(R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]DIRUTHENATE(II); 199684-47-4; 199541-17-8; Dimethylammonium dichlorotri(mu-chloro)bis[(R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]diruthenate(II), [NH2Me2][{RuCl((R)-binap)}2(mu-Cl)3]; (R)-[(RuCl(BINAP))2(mu-Cl)3[NH2Me2]; DIMETHYLAMMONIUM DICHLOROTRI(MU-CHLORO)BIS[(S)-(-)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]DIRUTHENATE(II); (R)-[(RuCl(BINAP))2(|I-Cl)3[NH2Me2];

IUPAC Name

[1-(2-diphenylphosphanylnaphthalen-1-yl)naphthalen-2-yl]-diphenylphosphane;N-methylmethanamine;ruthenium;trichloronioruthenium(1-);chloride;hydrochloride;

Molecular Weight

1673.882g/mol

Molecular Formula

C90H75Cl5NP4Ru2+;

Canonical SMILES

CNC.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8.Cl.[Cl-].[ClH+][Ru-]([ClH+])[ClH+].[Ru];

InChI

InChI=1S/2C44H32P2.C2H7N.5ClH.2Ru/c2*1-5-19-35(20-6-1)45(36-21-7-2-8-22-36)41-31-29-33-17-13-15-27-39(33)43(41)44-40-28-16-14-18-34(40)30-32-42(44)46(37-23-9-3-10-24-37)38-25-11-4-12-26-38;1-3-2;;;;;;;/h2*1-32H;3H,1-2H3;5*1H;;/q;;;;;;;;;+2/p-1;

InChI Key

NVDGOPZSESFSJS-UHFFFAOYSA-M;

Storage

2-8°C

Complexity

809

Covalently-Bonded Unit Count

Exact Mass

1676.136g/mol

Formal Charge

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

102

Monoisotopic Mass

1672.138g/mol

Rotatable Bond Count

Topological Polar Surface Area

12A^2

Application

The compound [NH2Me2][(RuCl((R)-binap))2(μ-Cl)3] serves as a precursor to Noyori catalyst systems, known for their exceptional catalytic activity and enantioselectivity in the hydrogenation of a variety of substrates. These systems are particularly effective in the highly enantioselective hydrogenation of functionalized ketones, accommodating substituents such as dialkylamino, hydroxy, siloxy, carbonyl, ester, amide, or thioester groups. Additionally, the corresponding ligand is versatile for use in several asymmetric catalytic processes, including the Heck reaction, palladium-catalyzed asymmetric arylation of ketones, rhodium-catalyzed 1,4-additions to enones, and other transformations such as hydroamination of styrene derivatives, Sakurai-Hosomi allylation, silver-catalyzed reactions, and asymmetric rearrangements. These properties make the compound a valuable tool in advancing applications in various asymmetric catalytic reactions.

January 29, 2025

Highly Effective Catalyst for Asymmetric Hydrogenation

I've used [NH2Me2][(RuCl((R)-binap))2(μ-Cl)3] in our lab's research on asymmetric hydrogenation. Its high enantioselectivity and efficiency with diverse substrates make it indispensable for optimizing our catalytic processes.