Chlorobis(cyclooctene)rhodium dimer

Chlorobis(cyclooctene)rhodium dimer is an organorhodium compound with the formula Rh₂Cl₂(C₈H₁₄)₄, where C₈H₁₄ is cis-cyclooctene. Sometimes abbreviated Rh₂Cl₂(coe)₄, it is a red-brown, air-sensitive solid that is a precursor to many other organorhodium compounds and catalysts.

Chlorobis(cyclooctene)rhodium dimer

Identifiers
CAS Number	12279-09-3
3D model (JSmol)	Interactive image
ChemSpider	21613963
ECHA InfoCard	100.152.028
PubChem CID	53384308
CompTox Dashboard (EPA)	DTXSID00693673
InChI InChI=1S/4C8H14.2ClH.2Rh/c4*1-2-4-6-8-7-5-3-1;;;;/h4*1-2H,3-8H2;2*1H;;/p-2/b4*2-1-;;;; Key: ZFCBAJWXKUDJSW-XFCUKONHSA-L
SMILES C1CCCC=CCC1.C1CCCC=CCC1.C1CCCC=CCC1.C1CCCC=CCC1.[Cl-].[Cl-].[Rh].[Rh]
Properties
Chemical formula	C32H56Cl2Rh2
Molar mass	717.50
Appearance	red-brown solid
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H315, H319, H332, H335
Precautionary statements	P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

The complex is prepared by treating an alcohol solution of hydrated rhodium trichloride with cyclooctene at room temperature.^[1] The coe ligands are easily displaced by other more basic ligands, more so than the diene ligands in the related complex cyclooctadiene rhodium chloride dimer.

Catalyst for C-H activation

C-H activation is often catalyzed by chlorobis(cyclooctene)rhodium dimer as demonstrated in the synthesis of a strained bicyclic enamine.^[2]

C–H bond activation Yotphan 2008

The synthesis of a mescaline analogue involves enantioselective annulation of an aryl imine via a C-H activation.^[3]

The total synthesis of lithospermic acid employs "guided C-H functionalization" late stage to a highly functionalized system. The directing group, a chiral nonracemic imine, is capable of performing an intramolecular alkylation, which allows for the rhodium-catalyzed conversion of imine to the dihydrobenzofuran.^[4]

Key step in synthesis of lithospermic acid