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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:
Molecular Weight:
717.50
MDL number:
UNSPSC Code:
12161600
PubChem Substance ID:
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

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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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)
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)
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)
Direct C-arylation of free (NH)-indoles and pyrroles catalyzed by Ar- Rh (III) complexes assembled in situ
Wang X, et al.
Journal of the American Chemical Society, 127(14), 4996-4997 (2005)
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

Articles

Discover the role of boronic acids in enantioenriched C(sp2)–C(sp2) product synthesis, specifically the rhodium-catalyzed Suzuki–Miyaura-type arylations of allylic halides and cyclobutenes.

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