Catalyst Ligands
Many of the tertiary phosphines sold as catalyst ligands are of a proprietary nature and are developed with the customer for one particular application. However, Cytec does offer "off the shelf" ligands under the CYTOP® organophosphine trade name such as CYTOP 355 - tricyclopentylphosphine and CYTOP 341 - triisobutylphosphine. The former is a potential alternate to tricyclohexylphosphine in the "Grubbs" catalyst. In addition, Cytec also offers several unique primary and secondary alkylphosphines such as CYTOP 266 - dicyclohexylphosphine, CYTOP 255 - dicyclopentylphosphine, CYTOP 241 - diisobutylphosphine, CYTOP 220 - dinorbornylphosphine and CYTOP 216 - 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phosphaadamantane. The 6-phenyl analogue of the latter is particularly effective as a ligand for Suzuki cross-coupling reactions. Such primary and secondary phosphines are useful intermediates for the synthesis of catalyst ligands.
Cytec's triarylphosphines (TOTP) and bidentate ligands (DPPB) have been used in a variety of catalytic applications in industrial and pharmaceutical industries. While both have application as hydroformylation catalyst ligands, they also find use in carbonylations, catalytic Heck and Suzuki couplings.
| Catalyst Ligand Photo Initiator |
| Product Name |
Chemical Name |
Format |
| CYTOP 208 organophosphine |
tris(3-hydroxypropyl)phosphine |
|
| CYTOP 216 organophosphine |
1,3,5,7-tetramethyl-2,4,8-trioxa-6-phosphaadamantane |
|
| CYTOP 222 organophosphine |
dinorbornylphosphine |
|
| CYTOP 255 organophosphine |
dicyclopentylphosphine |
|
| CYTOP 266 organophosphine |
dicyclohexylphosphine |
Download PDF |
| CYTOP 320 organophosphine |
triethylphosphine |
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| CYTOP 331 organophosphine |
tris(2-cyanoethyl)phosphine |
|
| CYTOP 340 organophosphine |
tri-n-butylphosphine |
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| CYTOP 341 organophosphine |
triisobutylphosphine |
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| CYTOP 360 organophosphine |
trihexylphosphine |
|
| CYTOP 366 organophosphine |
tricyclohexylphosphine |
|
| CYTOP 380 organophosphine |
tri-n-octylphosphine |
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| DPPB |
bis-1,4-(diphenylphosphino)butane |
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| DPPE |
bis-1,2-(diphenylphosphino)ethane |
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| DPPP |
bis-1,3-(diphenylphosphino)propane |
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| TOTP |
tri-o-tolylphosphine |
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|
| Catalyst Ligands Technical References |
| Category |
Journal |
Title |
Author |
| Carbonylation |
WO 199738964; Shell International Research |
Process for the carbonylation of ethylenically unsaturated compounds |
Drent, E.; De Castro, L.; Gilespie, H; Van Helden, A. and McKenna, E. |
| Hydroformylation |
Dalton (2003),2036-2042 |
Bicyclic phosphines as ligands for cobalt-catalysed hydroformylation |
Crause,C.; Bennie, L.; Damoense, L.; Dwyer, C.; Grove, C.;Grimmer, N.; Rensburg, W.; Kirk, M. M.; Mokheseng, S O. and Stynberg, P |
| Journal of Molecular Catalysis A: Chemical (1996), 112, 367-383 |
Functionalized phosphine substituted cobalt carbonyls. Synthesis, characterization and catalytic activity in the hydroformylation of olefins. |
Rosi L; Bini A; Frediani P; Bianchi M and Silvini A |
Suzuki Coupling
|
J. Org. Chem., (2004),69,5082-5086 |
Palladium Complexes of 1,3,5,7-Tetramethyl-2,4,8-trioxa-6-phenyl-6-phosphaadamantane: Synthesis, Chrystal Structure and Use in Suzuki and Sonogashira Reactions and the a-Arylation of Ketones |
Adjabeng, G.; Brenstrum,T.; Frampton,C.; Robertson, A.; Hillhouse, J. H.; McNulty, J and Capretta, A. |
| J. Org. Chem., (2004),69,5082-5086 |
Palladium Complexes of 1,3,5,7-Tetramethyl-2,4,8-trioxa-6-phenyl-6-phosphaadamantane: Synthesis, Chrystal Structure and Use in Suzuki and Sonogashira Reactions and the a-Arylation of Ketones |
Adjabeng, G.; Brenstrum,T.; Frampton,C.; Robertson, A.; Hillhouse, J. H.; McNulty, J and Capretta, A. |
Heck Coupling
|
Adv. Synth. Cata;., (2002),5,344 |
First application of secondary phosphines as supporting ligands for the palladium-catalyzed Heck reaction: Efficient activation of aryl chlorides |
Schnyder, A; Aemmer, T; Indolese, A; Pittelkow U and Studer M |
Synthesis of Catalyst Ligands
|
J. Org. Chem., (1961), 27, 1824 |
4-Phosphorinanones. II |
Welcher, W and Day, N |
| Review of Catalysts Ligands |
Synthesis, 2003,3,317-335 |
Alkyl Phosphines as Reagents and Catalysts in Organic Synthesis |
Valentine, D. and Hillhouse, J. |
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