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Bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate
PRICE INQUIRYCatalog Number
ACM99326348
Product Name
Bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate
Structure
![{[CurrentData.Name]}](https://resource.alfachemic.com/structure/99326-34-8.gif)
CAS
99326-34-8
Synonyms
(1Z,5Z)-cycloocta-1,5-diene;rhodium;trifluoromethanesulfonate
IUPAC Name
(1Z,5Z)-cycloocta-1,5-diene;rhodium;trifluoromethanesulfonate;
Molecular Weight
468.34
Molecular Formula
C17H24F3O3RhS
Canonical SMILES
C1CC=CCCC=C1.C1CC=CCCC=C1.C(F)(F)(F)S(=O)(=O)[O-].[Rh]
InChI
InChI=1S/2C8H12.CHF3O3S.Rh/c2*1-2-4-6-8-7-5-3-1;2-1(3,4)8(5,6)7;/h2*1-2,7-8H,3-6H2;(H,5,6,7);/p-1/b2*2-1-,8-7-;
InChI Key
VUTUHLLWFPRWMT-QMDOQEJBSA-M
Melting Point
159 °C
Purity
99%
Appearance
Red brown powder
Storage
Refrigerator (+4°C)
Color Form
crystalline
Complexity
217
Covalently-Bonded Unit Count
4
Defined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
4
Empirical Formula
[Rh(cod)2]CF3SO3
Exact Mass
468.04532
Formal Charge
-1
H-Bond Acceptor
6
Heavy Atom Count
25
Isomeric SMILES
C1/C=C\CC/C=C\C1.C1/C=C\CC/C=C\C1.C(S(=O)(=O)[O-])(F)(F)F.[Rh]
Metal Content
22
Monoisotopic Mass
468.04532
Rotatable Bond Count
0
Topological Polar Surface Area
65.6 Ų
Application
Bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate serves as a highly effective precatalyst for various rhodium-catalyzed chemical reactions. Its purpose is to facilitate complex organic transformations with high efficiency and selectivity. This compound is particularly valuable in asymmetric and cross-coupling catalysis, enabling precise control over the hydrogenative couplings of nonsymmetric 1,3-diynes to ethyl glyoxalate, as well as the reductive Mannich coupling of vinyl ketones to N-sulfonylimines mediated by hydrogen. Additionally, it plays a crucial role in the asymmetric synthesis of Sitagliptin and the hydrogenation of tetrasubstituted α,β-unsaturated ketones. Its application ensures precise regiocontrol and enantioselectivity in these sophisticated chemical processes.
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