Product Name :
2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (CAS 564483-18-7)

Synonym :
XPhos

Application :
2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl is a ligand for Buchwald-Hartwig Cross Coupling Reaction

CAS:
564483-18-7

Purity:
≥98%

Molecular Weight:
476.72

Formula :
C33H49P

Physical state:
Solid

solubility :
Soluble in water (partly).

Shipping Condition :
Store at room temperature

Melting point:
187-190° C

SMILES:
CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C

References:
:Insights into the origin of high activity and stability of catalysts derived from bulky, electron-rich monophosphinobiaryl ligands in the Pd-catalyzed C-N bond formation. | Strieter, ER., et al. 2003. J Am Chem Soc. 125: 13978-80. PMID: 14611232Significantly improved method for the pd-catalyzed coupling of phenols with aryl halides: understanding ligand effects. | Burgos, CH., et al. 2006. Angew Chem Int Ed Engl. 45: 4321-6. PMID: 16733839Dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine-dichlorophenylborane. | Braunschweig, H., et al. 2009. Acta Crystallogr Sect E Struct Rep Online. 65: o2787. PMID: 21578380Mixed phosphine/N-heterocyclic carbene palladium complexes: synthesis, characterization and catalytic use in aqueous Suzuki-Miyaura reactions. | Schmid, TE., et al. 2013. Dalton Trans. 42: 7345-53. PMID: 23348096Mechanistic switch in dual gold catalysis of diynes: C(sp(3))-H activation through bifurcation–vinylidene versus carbene pathways. | Hansmann, MM., et al. 2013. Angew Chem Int Ed Engl. 52: 2593-8. PMID: 23362151Organocatalytic reactions of alpha -trifluoromethylated esters with terminal alkenes at room temperature. | Wang, Q., et al. 2013. J Org Chem.957135-12-5 uses 78: 12525-31. PMID: 24251733Osmium(0)-Catalyzed C-C Coupling of Ethylene and alpha -Olefins with Diols, Ketols, or Hydroxy Esters via Transfer Hydrogenation. | Park, BY., et al. 2016. J Org Chem. 81: 8585-94. PMID: 27580269DFT Investigation of Suzuki-Miyaura Reactions with Aryl Sulfamates Using a Dialkylbiarylphosphine-Ligated Palladium Catalyst. | Melvin, PR., et al. 2017. Organometallics. 36: 3664-3675. PMID: 29805192Palladium-Catalyzed Direct alpha -C(sp3) Heteroarylation of Ketones under Microwave Irradiation.Buy1234616-13-7 | Quillen, A.PMID:33580859 , et al. 2019. J Org Chem. 84: 7652-7663. PMID: 31001979Environmentally Benign Strategy for Arylation of Nitronyl Nitroxide Using a Non-Transition Metal Nucleophile. | Suzuki, S., et al. 2020. Org Lett. 22: 1350-1354. PMID: 32011895Reductive C-C Coupling from Molecular Au(I) Hydrocarbyl Complexes: A Mechanistic Study. | Miranda-Pizarro, J., et al. 2021. J Am Chem Soc. 143: 2509-2522. PMID: 33544575Third Generation Buchwald Precatalysts with XPhos and RuPhos: Multigram Scale Synthesis, Solvent-Dependent Isomerization of XPhos Pd G3 and Quality Control by 1H- and 31P-NMR Spectroscopy. | Sotnik, SO., et al. 2021. Molecules. 26: PMID: 34207506Combined Experimental and Computational Mechanistic Investigation of the Palladium-Catalyzed Decarboxylative Cross-Coupling of Sodium Benzoates with Chloroarenes. | Humke, JN., et al. 2021. J Org Chem. 86: 11419-11433. PMID: 34339213