CAS 38465-86-0 (1,5-Cyclooctadiene)bis(methyldiphenylphosphine)iridium(I) hexafluorophosphate

Synonyms

(1Z,5Z)-Cycloocta-1,5-diene;iridium;methyl(diphenyl)phosphane;hexafluorophosphate

IUPAC Name

(1Z,5Z)-cycloocta-1,5-diene;iridium;methyl(diphenyl)phosphane;hexafluorophosphate;

Molecular Weight

845.8

Molecular Formula

C34H38F6IrP3

Canonical SMILES

CP(C1=CC=CC=C1)C2=CC=CC=C2.CP(C1=CC=CC=C1)C2=CC=CC=C2.C1CC=CCCC=C1.F[P-](F)(F)(F)(F)F.[Ir]

InChI

InChI=1S/2C13H13P.C8H12.F6P.Ir/c2*1-14(12-8-4-2-5-9-12)13-10-6-3-7-11-13;1-2-4-6-8-7-5-3-1;1-7(2,3,4,5)6;/h2*2-11H,1H3;1-2,7-8H,3-6H2;/q;-1;/b;2-1-,8-7-;

InChI Key

MUHONFFTSOCMDH-JXNOXZOESA-N

Melting Point

224 °C

Purity

97%

Appearance

Powder

Complexity

272

Covalently-Bonded Unit Count

Defined Bond Stereocenter Count

Exact Mass

846.17198

Formal Charge

-1

H-Bond Acceptor

Heavy Atom Count

Isomeric SMILES

CP(C1=CC=CC=C1)C2=CC=CC=C2.CP(C1=CC=CC=C1)C2=CC=CC=C2.C1/C=C\CC/C=C\C1.F[P-](F)(F)(F)(F)F.[Ir]

Monoisotopic Mass

846.17198

Rotatable Bond Count

Topological Polar Surface Area

0 Å²

Application

(1,5-Cyclooctadiene)bis(methyldiphenylphosphine)iridium(I) hexafluorophosphate is a red crystalline powder that serves as an air-stable cationic iridium complex, primarily utilized in allyl isomerization reactions. This compound, when dissolved and bubbled with hydrogen in solvents like tetrahydrofuran, transforms into an active catalyst, [IrH2(solv)2(PPh2Me)2]PF6. This catalyst is instrumental in the isomerization of various compounds, such as converting 3-(silyloxy)-1-propenylboronates into (γ-(silyloxy)allyl)boronic esters, diallyl ethers into allyl (E)-vinyl ethers, and 1-alkenylboronates into 3-alkoxyallylboronates, showcasing its versatility and efficiency in synthetic chemistry applications.

April 15, 2025

Reliable Iridium Catalyst for Allyl Isomerization Reactions

I used Alfa Chemistry's (1,5-Cyclooctadiene)bis(methyldiphenylphosphine)iridium(I) hexafluorophosphate for allyl isomerization. Its stability and effectiveness in forming active catalysts in tetrahydrofuran were impressive, enhancing the efficiency of complex synthesis processes.