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337455

Sigma-Aldrich

(1,5-Cyclooctadiene)bis(methyldiphenylphosphine)iridium(I) hexafluorophosphate

97%

Synonym(s):

[Ir(PMePh2)2COD]+ PF6-, [Ir(cod)(PPh2Me)2]PF6, {Ir(COD)[PCH3(C6H5)2]2}PF6

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About This Item

Empirical Formula (Hill Notation):
C34H38F6IrP3
CAS Number:
38465-86-0
Molecular Weight:
845.79
MDL number:
MFCD00064800
UNSPSC Code:
12161600
PubChem Substance ID:
24860482
NACRES:
NA.22

Assay

97%

reaction suitability

core: iridium
reagent type: catalyst

mp

224 °C (dec.) (lit.)

SMILES string

[Ir+].F[P-](F)(F)(F)(F)F.C1CC=CCCC=C1.CP(c2ccccc2)c3ccccc3.CP(c4ccccc4)c5ccccc5

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;+1/b;;2-1-,8-7-;;

InChI key

LXKHQEQLBSJJCO-JXNOXZOESA-N

Application

(1,5-Cyclooctadiene)bis(methyldiphenylphosphine)iridium(I) hexafluorophosphate is an air-stable cationic iridium complex, generally employed in allyl isomerization reactions. Upon bubbling hydrogen into the solution of [Ir(cod)(PPh2Me)2]PF6, preferably in tetrahydrofuran, results in the formation of active catalyst [IrH2(solv)2(PPh2Me)2]PF6 which can be used in the isomerization of 3-(silyloxy)-1-propenylboronates to (γ-(silyloxy)allyl)boronic esters; diallyl ethers to allyl (E)-vinyl ethers and 1-alkenylboronates to corresponding 3-alkoxyallylboronates.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - 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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Methyldiphenylphosphine 99%

Sigma-Aldrich

244902

Methyldiphenylphosphine

Synthesis of Chiral Esters of (E)-3-(Silyloxy)-2-propenylboronic Acid via the Iridium-Catalyzed Isomerization of the Double Bond.
Yamamoto Y, et al.
The Journal of Organic Chemistry, 64(1), 296-298 (1999)
Stereoselective Isomerization of Unsymmetrical Diallyl Ethers to Allyl (E)-Vinyl Ethers by a Cationic Iridium Catalyst.
Yamamoto Y, et al.
Synthetic Communications, 30(13), 2383-2391 (2000)
Intramolecular allylboration of γ-(?-formylalkoxy) allylboronates for syntheses of trans-or cis-2-(ethenyl) tetrahydropyran-3-ol and 2-(ethenyl) oxepan-3-ol.
Yamamoto Y, et al.
Tetrahedron, 59(4), 537-542 (2003)
Paulsen, H.; Adermann, K.
Carbohydrate Research, 175, 163-163 (1988)
Isomerisation of allyl ethers catalysed by the cationic iridium complex [Ir (cyclo-octa-1, 5-diene)(PMePh 2) 2] PF 6. A highly stereoselective route to trans-propenyl ethers.
Baudry D, et al.
Journal of the Chemical Society. Chemical Communications, (16), 694-695 (1978)
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