705945-70-6

Basic information

• Product Name: (R)-TCFP-RH
• Synonyms: (R)-(-)-T-BUTYLMETHYL(DI-T-BUTYLPHOSPHINOMETHYL)PHOSPHINO(1,5-CYCLOOCTADIENE)RHODIUM(I) TETRAFLUOROBORATE;(R)-TCFP-RH;(R)-(-)-t-Butylmethyl(di-t-butylphosphinomethyl)phosphino(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate, min. 97% (R)-TCFP-Rh;(R)-(-)-t-Butylmethyl(di-t-butylphosphinomethyl)phosphino(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate, min. 97% (R)-TCFP-Rh;(R)-(-)-t-ButylMethyl(di-t-butylphosphinoMethyl)phosphino(1,5-cyclooctadiene)rhodiuM(I) tetrafluoroborate,97% (R)-TCFP-Rh;(R)-(-)-t-ButylMethyl(di-t-butylphosphinoMethyl)phosphino(1,5-cyclooctadiene);(R)-[Rh COD TCFP]BF4, Rh 18.4%
• CAS NO: 705945-70-6
• Molecular Formula: BF₄*C₂₂H₄₄P₂Rh
• Molecular Weight: 368.516402
• Product Categories: organometallic complex;Rh
• Mol File: 705945-70-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: -69.5
• Boiling Point: 151
• Appearance: yellow to orange/Powder
• Density: 0.88
• Sensitive: Air Sensitive
• CAS DataBase Reference: (R)-TCFP-RH(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-TCFP-RH(705945-70-6)
• EPA Substance Registry System: (R)-TCFP-RH(705945-70-6)

Safety Data

• Hazardous Substances Data: 705945-70-6(Hazardous Substances Data)

Usage

Reaction

Catalyst for highly enantioselective, rapid, hydrogenation of α and β-acetamido dehydroaminoacids and related enamides and unsaturated acids.

InChI:InChI=1S/C8H12/c1-2-4-6-8-7-5-3-1/h1-2,7-8H,3-6H2/b2-1-,8-7-

Upstream product

• 35138-22-8 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 
• 705945-65-9 P(CH₃)C(CH₃)3CH₂P(C(CH₃)3)2 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 705945-65-9 P(CH₃)C(CH₃)3CH₂P(C(CH₃)3)2 
• 705945-65-9 (R)-tert-butylmethylphosphino-di-tert-butylphosphinomethane 

Downstream Products

• 1008533-32-1 (Rh(((CH₃)3C)2PCH₂P(CH₃)(C(CH₃)3))(CH₃CONHC(COOCH₃)CHC₆H₅))⁽¹⁺⁾ 
• 1008533-33-2 (Rh(((CH₃)3C)2PCH₂P(CH₃)(C(CH₃)3))(CH₃CONHC(COOCH₃)CHC₆H₅))⁽¹⁺⁾ 

Relevant articles and documents

PROCESS FOR PREPARING CATIONIC RHODIUM COMPLEXES

A process is described for the synthesis of a cationic [rhodium diolefin phosphorus ligand] complex comprising the steps of: (a) reacting a rhodium-diolefin-1,3-diketonate and an acid in a ketone solvent, (b) adding a stabilising olefin to form a stabilised cationic rhodium compound, and (c) mixing a phosphorus ligand with the solution of the stabilised cationic rhodium compound to form a solution of the cationic [rhodium diolefin phosphorus ligand] complex. The solution may be used directly or the complex recovered. In one embodiment, the solution may be combined with a co-solvent and the ketone removed to give a new catalyst solution, from which the complex may be recovered.

Highly Selective Asymmetric Hydrogenation Using a Three Hindered Quadrant Bisphosphine Rhodium Catalyst

A concise synthesis of both enantiomers of ligand 2 and rhodium complex 5 is presented. The crux of the synthesis is a chiral HPLC separation of the enantiomers of 4. Rhodium complex 5 possesses three hindered quadrants in the steric environment within which a substrate binds. Evidence is presented that this configuration leads to high enantioselectivity (>99% ee) for rhodium-catalyzed asymmetric hydrogenation of α-acetamido dehydroamino acids, 6a-e. High enantioselectivities are also reported for the hydrogenation of a substrate precursor, 8, of pharmaceutical candidate, pregabalin. Advantages for large-scale hydrogenation of 8 using catalyst 5a vs Rh-Me-DuPhos are discussed. Copyright