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685062

Sigma-Aldrich

(1,5-Cyclooctadiene)(methoxy)iridium(I) dimer

Synonym(s):

[Ir(OMe)(1,5-cod)]2, Bis(1,5-cyclooctadiene)di-μ-methoxydiiridium(I)

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About This Item

Linear Formula:
[Ir(OCH3)(C8H12)]2
CAS Number:
12148-71-9
Molecular Weight:
662.86
MDL number:
MFCD08459360
UNSPSC Code:
12161600
PubChem Substance ID:
329760940
NACRES:
NA.22

form

crystals

Quality Level

100

reaction suitability

core: iridium
reagent type: catalyst
reaction type: C-H Activation

mp

154-179 °C (D)

storage temp.

−20°C

SMILES string

C[O+]1[Ir-]2[O+](C)[Ir-]12.C3CC=CCCC=C3.C4CC=CCCC=C4

InChI

1S/2C8H12.2CH3O.2Ir/c2*1-2-4-6-8-7-5-3-1;2*1-2;;/h2*1-2,7-8H,3-6H2;2*1H3;;/q;;2*+1;2*-1/b2*2-1-,8-7-;;;;

InChI key

BGWIAAATAAWGOI-MIXQCLKLSA-N

Application

Catalyst for:
  • Preparation of heteroaryl fused indole ring systems as inhibitors of HCV NS5B polymerase
  • Borylation/Suzuki-Miyaura coupling
  • Metalation-Suzuki cross-coupling procedure for the synthesis of biaryls and heterobiaryls
  • Tetraborylation reactions
  • Highly regio- and enantioselective asymmetric hydroboration
  • Ortho-silylation of aryl ketone, benzaldehyde, and benzyl alcohol derivatives via C-H activation
A powerful C-H activation catalyst to prepare phenols from arenes

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Direct C?H borylation and C?H arylation of pyrrolo [2, 3-d] pyrimidines: synthesis of 6, 8-disubstituted 7-deazapurines.
Klecka M, et al.
Organic & Biomolecular Chemistry, 7(5), 866-868 (2009)
Catalytic functionalization of unactivated primary C?H bonds directed by an alcohol.
Simmons E, et al.
Nature, 483(7387), 70-70 (2012)
Ir?Catalyzed Borylation of C H Bonds in N?Containing Heterocycles: Regioselectivity in the Synthesis of Heteroaryl Boronate Esters.
Mkhalid I, et al.
Angewandte Chemie (International Edition in English), 45(3), 489-491 (2006)
A general strategy for the perfluoroalkylation of arenes and arylbromides by using arylboronate esters and [(phen) CuRF].
Litvinas N, et al.
Angewandte Chemie (International Edition in English), 51(2), 536-539 (2012)
Robert E Maleczka et al.
Journal of the American Chemical Society, 125(26), 7792-7793 (2003-06-26)
An efficient one-pot C-H activation/borylation/oxidation protocol for the preparation of phenols is described. This method is particularly attractive for the generation of meta-substituted phenols bearing ortho-/para-directing groups, as such substrates are difficult to access by other phenol syntheses.

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