Wilkinson's catalyst

Wilkinson's catalyst
Names
	IUPAC name (SP-4)-chloridotris(triphenylphosphene)rhodium
	Other names Rhodium(I) tris(triphenylphosphene) chloride,; Wilkinson's catalyst,; Tris(triphenylphosphene)rhodium(I) chloride
Identifiers
CAS Number	14694-95-2 ;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.035.207
EC Number	238-744-5;
PubChem CID	84599;
RTECS number	none;
UNII	0FV534BKEV ;
CompTox Dashboard (EPA)	DTXSID30893902 ;
	InChI InChI=1S/3C18H15P.ClH.Rh/c31-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;;/h31-15H;1H;/p-1 Key: QBERHIJABFXGRZ-UHFFFAOYSA-M;
	SMILES Cl[Rh-3]([P+](c0ccccc0)(c0ccccc0)c0ccccc0)([P+](c0ccccc0)(c0ccccc0)c0ccccc0)[P+](c0ccccc0)(c0ccccc0)c0ccccc0;
Properties
Chemical formula	C54H45ClP3Rh
Molar mass	925.22 g/mol
Appearance	red solid
Melting point	245 to 250 °C (473 to 482 °F; 518 to 523 K)
Solubility in water	insoluble in water
Solubility in other solvents	20 g/L (CHCl3, CH2Cl2), 2 g/L (benzene, toluene)
Structure
Coordination geometry	square planar d8 (diamagnetic; sp2d-hybridized)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	none
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H317, H413
Precautionary statements	P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P330, P333+P313, P363, P501
Related compounds
Related compounds	triphenylphosphene; Pd(PPh3)4; IrCl(CO)[P(C6H5)3]2
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Wilkinson's catalyst (chloridotris(triphenylphosphine)rhodium(I)) is a coordination complex of rhodium with the formula [RhCl(PPh₃)], where 'Ph' denotes a phenyl group. It is a red-brown colored solid that is soluble in hydrocarbon solvents such as benzene, and more so in tetrahydrofuran or chlorinated solvents such as dichloromethane. The compound is widely used as a catalyst for hydrogenation of alkenes. It is named after chemist and Nobel laureate Sir Geoffrey Wilkinson, who first popularized its use.

Historically, Wilkinson's catalyst has been a paradigm in catalytic studies leading to several advances in the field such as the implementation of some of the first heteronuclear magnetic resonance studies for its structural elucidation in solution (³¹P),^[3] parahydrogen-induced polarization spectroscopy to determine the nature of transient reactive species,^[4] or one of the first detailed kinetic investigation by Halpern to elucidate the mechanism.^[5] Furthermore, the catalytic and organometallic studies on Wilkinson's catalyst also played a significant role on the subsequent development of cationic Rh- and Ru-based asymmetric hydrogenation transfer catalysts which set the foundations for modern asymmetric catalysis.^[6]

^ Cite error: The named reference IS was invoked but never defined (see the help page).
^ "Chlorotris(triphenylphosphine)rhodium(I)". pubchem.ncbi.nlm.nih.gov.
^ Meakin, P.; Jesson, J. P.; Tolman, C. A. (1 May 1972). "Nature of chlorotris(triphenylphosphene)rhodium in solution and its reaction with hydrogen". Journal of the American Chemical Society. 94 (9): 3240–3242. doi:10.1021/ja00764a061. ISSN 0002-7863.
^ Duckett, Simon B.; Newell, Connie L.; Eisenberg, Richard (1994). "Observation of New Intermediates in Hydrogenation Catalyzed by Wilkinson's Catalyst, RhCl(PPh3)3, Using Parahydrogen-Induced Polarization". Journal of the American Chemical Society. 116 (23): 10548–10556. doi:10.1021/ja00102a023.
^ Halpern, Jack (1 January 1981). "Mechanistic aspects of homogeneous catalytic hydrogenation and related processes". Inorganica Chimica Acta. 50: 11–19. doi:10.1016/S0020-1693(00)83716-0.
^ Hartwig, John F. (2010). Organotransition metal chemistry- From bonding to Catalysis. University Science Books. ISBN 978-1-891389-53-5.

[IS-1] Cite error: The named reference IS was invoked but never defined (see the help page).

[2] "Chlorotris(triphenylphosphine)rhodium(I)". pubchem.ncbi.nlm.nih.gov.

[3] Meakin, P.; Jesson, J. P.; Tolman, C. A. (1 May 1972). "Nature of chlorotris(triphenylphosphene)rhodium in solution and its reaction with hydrogen". Journal of the American Chemical Society. 94 (9): 3240–3242. doi:10.1021/ja00764a061. ISSN 0002-7863.

[4] Duckett, Simon B.; Newell, Connie L.; Eisenberg, Richard (1994). "Observation of New Intermediates in Hydrogenation Catalyzed by Wilkinson's Catalyst, RhCl(PPh3)3, Using Parahydrogen-Induced Polarization". Journal of the American Chemical Society. 116 (23): 10548–10556. doi:10.1021/ja00102a023.

[5] Halpern, Jack (1 January 1981). "Mechanistic aspects of homogeneous catalytic hydrogenation and related processes". Inorganica Chimica Acta. 50: 11–19. doi:10.1016/S0020-1693(00)83716-0.

[6] Hartwig, John F. (2010). Organotransition metal chemistry- From bonding to Catalysis. University Science Books. ISBN 978-1-891389-53-5.

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