Cas no 705945-68-2 ((S)-[Rh COD TCFP]BF4)

(S)-[Rh(COD)(TCFP)]BF? is a chiral rhodium(I) complex featuring a cyclooctadiene (COD) ligand and a tetrakis(trifluoromethyl)phenyl (TCFP) phosphine group. This catalyst is particularly valued for its high enantioselectivity in asymmetric hydrogenation and C–C bond-forming reactions, making it useful in fine chemical and pharmaceutical synthesis. The electron-withdrawing TCFP ligand enhances the rhodium center's electrophilicity, improving reactivity with sterically demanding substrates. The BF?? counterion ensures good solubility in polar organic solvents. Its well-defined structure and air stability in solid form facilitate handling and reproducibility. This complex is a preferred choice for stereocontrolled transformations requiring precise chiral induction.
(S)-[Rh COD TCFP]BF4 structure
(S)-[Rh COD TCFP]BF4 structure
Product Name:(S)-[Rh COD TCFP]BF4
CAS No:705945-68-2
MF:C22H44BF4P2Rh
MW:560.242404937744
CID:1745043
PubChem ID:72376358
Update Time:2025-10-25

(S)-[Rh COD TCFP]BF4 Chemical and Physical Properties

Names and Identifiers

    • (S)-(+)-t-Butylmethyl(di-t-butylphosphinomethyl)phosphino(1,5- cyclooctadiene)rhodium(I) tetrafluoroborate
    • Suvorexant [USAN:INN]
    • MK4305
    • [(R)-4-(5-chlorobenzoxazol-2-yl)-7-methyl-[1,4]diazepan-1-yl]-(5-methyl-2-[1,2,3]triazol-2-yl-phenyl)methanone
    • MK-4305
    • [((R)-trichickenfootphos)Rh(cod)]BF4
    • [(R)-4-(5-chlorobenzooxazol-2-yl)-7-methyl-[1,4]diazepan-1-yl](5-methyl-2-[1,2,3]triazol-2-yl-phenyl)methanone
    • Suvorexant
    • ((7R)-4-(5-Chloro-1,3-benzoxazol-2-yl)-7-methyl-1,4-diazepan-1-yl)(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone
    • (S)-[Rh(COD)(TCFP)]BF4
    • DORA-analogue
    • [(7R)-4-(5-chloro-1,3-benzoxazol-2-yl)-7-methyl-1,4-diazepan-1-yl][5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl]methanone
    • UNII-081L192FO9
    • (S)-(+)-(2-{[(di-t-butylphosphanyl)methyl]methylphosphanyl}-2-methylpropane)-(1,5-cyclooctadiene)rhodium (I) tetrafluroborate
    • 5-chloro-2-{(5R)-5-methyl-4-[5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoyl]-1,4-diazepan-1-yl}-1,3-benzoxazole
    • [(R)-TCFP-Rh]
    • (S)-[RH COD TCFP]BF4, RH 18.4
    • (S)-[Rh COD TCFP]BF4
    • (S)-(+)-T-BUTYLMETHYL(DI-T-BUTYLPHOSPHINOMETHYL)PHOSPHINO(1,5-CYCLOOCTADIENE)RHODIUM(I) TETRAFLUOROBORATE
    • SC10394
    • (R)-(-)-T-BUTYLMETHYL(DI-T-BUTYLPHOSPHINOMETHYL)PHOSPHINO(1,5-CYCLOOCTADIENE)RHODIUM(I) TETRAFLUOROBORATE;(R)-TCFP-RH;[(R-TERT-BUTYLMETHYLPHOSPHINO-DI-TERT-BUTYLPHOSPHINOMETHANE)(1,5-CYCLOOCTADIENE)RHODIUM(I)] TETRAFLUOROBORATE;(S)-(+)-t-Butylmethyl(di-t-butylphosphinomethyl)phosphino(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate
    • MFCD11973806
    • 705945-68-2
    • Inchi: 1S/C14H32P2.C8H12.BF4.Rh/c1-12(2,3)15(10)11-16(13(4,5)6)14(7,8)9;1-2-4-6-8-7-5-3-1;2-1(3,4)5;/h11H2,1-10H3;1-2,7-8H,3-6H2;;/q;;-1;/b;2-1-,8-7-;;/t15-;;;/m0.../s1
    • InChI Key: CRUGJRKRRYVPDF-ZRXYBOGPSA-N
    • SMILES: [Rh].P(C[P@](C)C(C)(C)C)(C(C)(C)C)C(C)(C)C.F[B-](F)(F)F.C1C=CCCC=CC1 |c:20,24|

Computed Properties

  • Exact Mass: 560.20000
  • Monoisotopic Mass: 560.20024g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 30
  • Rotatable Bond Count: 5
  • Complexity: 290
  • Covalently-Bonded Unit Count: 4
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 2
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 0

Experimental Properties

  • Melting Point: 171-177 °C
  • PSA: 27.18000
  • LogP: 10.32570

(S)-[Rh COD TCFP]BF4 Pricemore >>

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Additional information on (S)-[Rh COD TCFP]BF4

Introduction to (S)-[Rh COD TCFP]BF4 and Its Significance in Modern Catalysis

The compound with the CAS number 705945-68-2 represents a fascinating advancement in the field of catalysis, particularly in the realm of chiral transition metal complexes. Among these, the product name (S)-[Rh COD TCFP]BF4 stands out due to its unique structural and functional properties. This introduction delves into the characteristics of this compound, its applications, and its relevance to the latest research findings in catalysis and related areas.

The central metal in this complex is rhodium, a member of the early transition metals known for their exceptional catalytic properties. The coordination environment of rhodium is critically influenced by the ligands attached to it. In the case of (S)-[Rh COD TCFP]BF4, the ligands play a pivotal role in determining the reactivity and selectivity of the complex. The bidentate ligand COD (1,5-cyclooctadiene) provides a stable five-membered chelate ring, while the tridentate ligand TCFP (1,3,5-tris(2-furyl)phosphine) introduces additional steric and electronic effects that modulate the catalytic activity.

The presence of the tetrafluoroborate anion (BF4-) as a counterion further enhances the stability of the complex, making it suitable for a wide range of applications. The chiral nature of the complex, indicated by the (S) configuration, is particularly significant in asymmetric catalysis, where enantioselective transformations are highly valued. Recent studies have demonstrated that (S)-[Rh COD TCFP]BF4 exhibits remarkable performance in various catalytic reactions, including hydrogenation, transfer hydrogenation, and C–C bond formation.

One of the most compelling aspects of this compound is its application in asymmetric hydrogenation reactions. These reactions are crucial in pharmaceutical synthesis, where enantiomerically pure compounds are often required. The use of (S)-[Rh COD TCFP]BF4 has shown excellent enantioselectivity in hydrogenating prochiral alkenes and ketones, leading to high yields of optically active products. This capability is particularly valuable in the synthesis of chiral drugs, where even small impurities can significantly impact biological activity.

Moreover, recent research has highlighted the utility of (S)-[Rh COD TCFP]BF4 in cross-coupling reactions, which are fundamental transformations in organic synthesis. The complex has been employed in Suzuki-Miyaura and Heck couplings, demonstrating high efficiency and selectivity. These reactions are widely used in constructing complex molecular architectures, including those found in natural products and pharmaceuticals. The ability to perform these reactions under mild conditions makes (S)-[Rh COD TCFP]BF4 an attractive catalyst for industrial applications.

The structural features of (S)-[Rh COD TCFP]BF4 also make it a promising candidate for studying fundamental catalytic mechanisms. The combination of computational methods and experimental techniques has provided valuable insights into how this complex interacts with substrates and how ligand effects influence catalytic performance. These studies not only enhance our understanding of transition metal catalysis but also pave the way for designing more efficient catalysts.

In conclusion, (S)-[Rh COD TCFP]BF4 represents a significant advancement in catalytic chemistry. Its unique combination of structural features and functional properties makes it highly effective in various catalytic applications, particularly in asymmetric hydrogenation and cross-coupling reactions. As research continues to uncover new applications and mechanisms related to this compound, its importance in modern synthetic chemistry is likely to grow even further.

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