CAS 64536-78-3 (1,5-Cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) Hexafluorophosphate

Synonyms

Felkin-crabtree catalyst; pyridine; (1,5-Cyclooctadiene)(pyridine)(tricyclohexylphosphine)-iridium(I) hexafluorophosphate, >=99.0% (C); (Tricyclohexylphosphine)(1,5-cyclooctadiene)(pyridine)iridium(I) hexafluorophosphate, 99%; (1Z,5Z)-cycloocta-1,5-diene; UNII-816RS2NBPN; ((1,2,5,6-eta)-1,5-Cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(1+) hexafluorophosphate(1-); C18H33P.C8H12.C5H5N.F6P.Ir; (TRICYCLOHEXYPHOSPHINE)(1,5-CYCLOOCTADIENE)(PYRIDINE)IRIDIUM(I) HEXAFLUOROPHOSPHATE; SC-67688;

IUPAC Name

(1Z,5Z)-cycloocta-1,5-diene;iridium;pyridine;tricyclohexylphosphane;hexafluorophosphate;

Molecular Weight

804.903g/mol

Molecular Formula

C31H50F6IrNP2-;

Canonical SMILES

C1CCC(CC1)P(C2CCCCC2)C3CCCCC3.C1CC=CCCC=C1.C1=CC=NC=C1.F[P-](F)(F)(F)(F)F.[Ir];

InChI

InChI=1S/C18H33P.C8H12.C5H5N.F6P.Ir/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;1-2-4-6-8-7-5-3-1;1-2-4-6-5-3-1;1-7(2,3,4,5)6;/h16-18H,1-15H2;1-2,7-8H,3-6H2;1-5H;;/q;;;-1;/b;2-1-,8-7-;;;;

InChI Key

WLRQNTYCIFESRH-KJWGIZLLSA-N;

Storage

2-8°C

Complexity

368

Covalently-Bonded Unit Count

Defined Bond Stereocenter Count

Exact Mass

805.295g/mol

Formal Charge

-1

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

805.295g/mol

Rotatable Bond Count

Topological Polar Surface Area

12.9A^2

UNII

816RS2NBPN

Application

(1,5-Cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) hexafluorophosphate is primarily used as a versatile catalyst in various chemical reactions. Its applications include the hydrogenation of substrates that are mono-, di-, tri-, and tetra-substituted, as well as in the isomerization and hydroboration of alkenes. This catalyst is integral in isotope exchange reactions, facilitating the direct exchange of hydrogen with its isotopes, deuterium and tritium. Moreover, it is renowned for its highly regioselective hydrogenation capabilities, especially in processes directed by carbonyl groups, using the Crabtree catalyst. In more specialized applications, it is utilized for the highly enantioselective hydrogenation of α,β-unsaturated esters, the stereoselective catalytic hydrogenation and conjugate reduction of 4-methylitaconate derivatives with chiral auxiliaries, and the synthesis of thiophene-based TAK-779 analogues through C-H arylation. Additionally, it plays a role in the synthesis of chiral (α-chloroalkyl)boronic esters via chemoselective hydrogenation of chloro-substituted alkenyl boronates, and it is effective in regioselective C-H activation and hydrogen-isotope exchange within non-aromatic unsaturated functionalities.

January 24, 2025

Fantastic Catalyst for Diverse Chemical Applications

I've been utilizing (1,5-Cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) Hexafluorophosphate from Alfa Chemistry for hydrogen isotope exchange and regioselective hydrogenation. Its reliable performance makes it indispensable in our lab's synthesis protocols.