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302473

Sigma-Aldrich

Chlorobis(cyclooctene)rhodium(I),dimer

98%

Synonym(s):

[Rh(coe)2Cl]2

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About This Item

Empirical Formula (Hill Notation):
C32H56Cl2Rh2
CAS Number:
12279-09-3
Molecular Weight:
717.50
MDL number:
MFCD00013287
UNSPSC Code:
12161600
PubChem Substance ID:
24858255
NACRES:
NA.22

Assay

98%

form

powder

reaction suitability

core: rhodium
reagent type: catalyst

mp

190 °C (dec.) (lit.)

SMILES string

Cl[Rh].Cl[Rh].C1CCCC=CCC1.C2CCCC=CCC2.C3CCCC=CCC3.C4CCCC=CCC4

InChI

1S/4C8H14.2ClH.2Rh/c4*1-2-4-6-8-7-5-3-1;;;;/h4*1-2H,3-8H2;2*1H;;/q;;;;;;2*+1/p-2/b4*2-1-;;;;

InChI key

GQPAPAIPOLEZHT-XFCUKONHSA-L

Application

Chlorobis(cyclooctene)rhodium(I),dimer can be used as a catalyst:
  • To synthesize enantioenriched gem-diaryl sulfonates by asymmetric 1,4-addition of aryl boronic acids to α,β-unsaturated sulfonyl compounds.
  • In direct C-arylation of N-unprotected indoles and pyrroles.
  • In the carboxylation of arenes via C-H bond activation.

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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Annulation of alkenyl-substituted heterocycles via rhodium-catalyzed intramolecular C-H activated coupling reactions.
K L Tan et al.
Journal of the American Chemical Society, 123(11), 2685-2686 (2001-07-18)
Ru-, Rh-, and Pd-catalyzed C-C bond formation involving C-H activation and addition on unsaturated substrates: reactions and mechanistic aspects.
Vincent Ritleng et al.
Chemical reviews, 102(5), 1731-1770 (2002-05-09)
Jay A Labinger et al.
Nature, 417(6888), 507-514 (2002-05-31)
The selective transformation of ubiquitous but inert C H bonds to other functional groups has far-reaching practical implications, ranging from more efficient strategies for fine chemical synthesis to the replacement of current petrochemical feedstocks by less expensive and more readily
Fumitoshi Kakiuchi et al.
Accounts of chemical research, 35(10), 826-834 (2002-10-16)
The cleavage and addition of ortho C-H bonds in various aromatic compounds such as ketones, esters, imines, imidates, nitrile, and aldehydes to olefins and acetlylenes can be achieved catalytically with the aid of ruthenium catalysts. The reaction is generally highly
Chiral Phosphite-Olefin Ligands: Application in Rh-Catalyzed Asymmetric 1, 4-Addition of Arylboronic Acids to beta-Aryl-alpha, beta-unsaturated Sulfonates
Yue-Na Y and Ming-Hua X
Acta Chimica Sinica , 72(7), 815-819 (2014)
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Articles

Direct Arylation of Heterocycles

Lewis and co-workers have recently disclosed a highly functional-group compatible Rh-catalyzed C-H bond activation for the rapid synthesis of functionalized heterocycles.

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