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905607

Sigma-Aldrich

(R)-Tol-BINAP Pd G3

≥95%

Synonym(s):

(R)-Tol-BINAP G3 palladacycle, (R)-Tol-BINAP palladacycle

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About This Item

Empirical Formula (Hill Notation):
C61H53NO3P2PdS
Molecular Weight:
1048.51
UNSPSC Code:
12352300

assay

≥95%

form

powder or crystals

feature

generation 3

reaction suitability

core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: catalyst
reaction type: Cross Couplings

mp

>300 °C

functional group

phosphine

SMILES string

PC1=CC=C2C(C=CC=C2)=C1C3=C(C)C=CC4=C3C=CC=C4.NC(C=CC=C5)=C5C6=C([Pd]OS(C)(=O)=O)C=CC=C6.[Tol2].[Tol2].P

Related Categories

General description

(R)-Tol-BINAP Pd G3 is a third generation (G3) Buchwald precatalyst. It is air, moisture and thermally stable and is highly soluble in a wide range of common organic solvents. It has long life in solutions. Qphos Pd G3 is an excellent reagent for palladium catalyzed cross-coupling reactions. Some of its unique features include lower catalyst loadings, shorter reaction time, efficient formation of the active catalytic species and accurate control of ligand: palladium ratio.

Application

(R)-Tol-BINAP Pd G3 can be used in the stereoselective synthesis of perfluoroalkyl-substituted enones by reacting four components, alkynes, iodoperfluoroalkanes, (hetero)arylboronic acids, and carbon monoxide.

Other Notes

Pd-Catalyzed Carbonylative Carboperfluoroalkylation of Alkynes. Through-Space 13C–19F Coupling as a Probe for Configuration Assignment of Fluoroalkyl-Substituted Olefins

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Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Sylwester Domański et al.
The Journal of organic chemistry, 82(15), 7998-8007 (2017-07-06)
A four-component Pd-catalyzed protocol for direct synthesis of perfluoroalkyl-substituted enones is reported. Under mild conditions and low catalyst loading, alkynes, iodoperfluoroalkanes, (hetero)arylboronic acids, and carbon monoxide are assembled into highly elaborate products with good yields and excellent regio- and stereoselectivities.
Pd-Catalyzed Carbonylative Carboperfluoroalkylation of Alkynes. Through-Space 13C-19F Coupling as a Probe for Configuration Assignment of Fluoroalkyl-Substituted Olefins.
Domanski S, et al.
The Journal of Organic Chemistry, 82(15), 7998-8007 (2017)

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