CAS 12112-67-3 Chloro(1,5-cyclooctadiene)iridium(I) dimer

Synonyms

Bis(1,5-cyclooctadiene)diiridium(I) dichloride

IUPAC Name

(1Z,5Z)-cycloocta-1,5-diene;iridium;dichloride;

Molecular Weight

671.71

Molecular Formula

C16H24Cl2Ir2

Canonical SMILES

C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Ir].[Ir]

InChI

InChI=1S/2C8H12.2ClH.2Ir/c2*1-2-4-6-8-7-5-3-1;/h2*1-2,7-8H,3-6H2;2*1H;/p-2/b2*2-1-,8-7-;

InChI Key

SHZHQWGWORCBJK-MIXQCLKLSA-L

Melting Point

205 °C

Purity

99%

Appearance

Red brown powder

Storage

2-8°C

Complexity

72.6

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

Defined Bond Stereocenter Count

EC Number

235-170-7

Exact Mass

670.04902

Formal Charge

-2

H-Bond Acceptor

Heavy Atom Count

Isomeric SMILES

C1/C=C\CC/C=C\C1.C1/C=C\CC/C=C\C1.[Cl-].[Cl-].[Ir].[Ir]

Monoisotopic Mass

672.05135

Rotatable Bond Count

Topological Polar Surface Area

0 Å²

Application

The compound Chloro(1,5-cyclooctadiene)iridium(I) dimer, characterized by its red-orange solid form, serves as a versatile precursor to a variety of iridium complexes used extensively in homogeneous catalysis. This compound is essential in facilitating numerous catalytic reactions, including carbonylation, hydrosilylation, hydroformylation, and asymmetric allylic substitutions, as well as metathesis and chiral catalysis. It plays a pivotal role in the synthesis of Crabtree's catalyst, utilized in hydrogenation and hydrogen-transfer reactions. The product is crucial for developing catalysts used in specific processes such as asymmetric hydrogenation of tri- and tetrasubstituted olefins, enantioselective reduction of imines, allylic alkylation, allylic amination and etherification, as well as the conversion of aroyl chlorides with internal alkynes into substituted naphthalenes and anthracenes. Furthermore, it facilitates the Ir-catalyzed addition of acid chlorides to terminal alkynes and promotes intramolecular hydroamination of unactivated alkenes with secondary alkyl- and arylamines. It is also instrumental in enantioselective [2+2] cycloaddition, silyl-directed ortho-borylation of arenes, cross-coupling of styrene derivatives with allylic carbonates, and transfer hydrogenative C-C coupling, showcasing its broad applicability and importance in advanced chemical synthesis.

January 4, 2025

Exceptional Catalytic Precursor for Advanced Applications

Chloro(1,5-cyclooctadiene)iridium(I) dimer from Alfa Chemistry is a game-changer in my research. It effectively catalyzed allylic alkylation and hydrogen-transfer reactions, streamlining our synthesis processes with remarkable efficiency. Highly recommend for complex catalyst preparations.