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rac-BINAP Pd G4

Synonym(s):

(Methanesulfonatato-κO)[2′-(methylamino-κN)-2-biphenylyl-κC2]palladium - 1,1′-binaphthalene-2,2′-diylbis(diphenylphosphine)

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About This Item

Empirical Formula (Hill Notation):
C58H47NO3P2PdS
CAS Number:
1599466-90-6
Molecular Weight:
1006.43
UNSPSC Code:
12161600
PubChem Substance ID:
329769806
NACRES:
NA.22

form

powder

Quality Level

100

feature

generation 4

reaction suitability

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

functional group

phosphine

InChI

1S/C44H32P2.C13H12N.CH4O3S.Pd/c1-5-19-35(20-6-1)45(36-21-7-2-8-22-36)41-31-29-33-17-13-15-27-39(33)43(41)44-40-28-16-14-18-34(40)30-32-42(44)46(37-23-9-3-10-24-37)38-25-11-4-12-26-38;1-14-13-10-6-5-9-12(13)11-7-3-2-4-8-11;1-5(2,3)4;/h1-32H;2-7,9-10,14H,1H3;1H3,(H,2,3,4);/q;;;+1/p-1

InChI key

JCAKNOAUMBTXEM-UHFFFAOYSA-M

Application

A powerful ligand for classic cross-coupling reactions combined with the Buchwald Fourth Generation Palladacycle. Bench stable, soluble in most organic solvents.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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Sandra M King et al.
Organic letters, 18(16), 4128-4131 (2016-08-09)
A general method for the N-arylation of amino acid esters with aryl triflates is described. Both α- and β-amino acid esters, including methyl, tert-butyl, and benzyl esters, are viable substrates. Reaction optimization was carried out by design of experiment (DOE)

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G3 and G4 Buchwald Precatalysts

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The Buchwald group has developed a series of highly active and versatile palladium precatalysts and biarylphosphine ligands used in cross-coupling reactions for the formation of C-C, C–N, C–O, C–F, C–CF3, and C–S bonds. The ligands are electron-rich, and highly tunable to provide catalyst systems with a diverse scope, high stability and reactivity. Furthermore, the new series of precatalysts are air-, moisture and thermally-stable and display good solubility in common organic solvents. The use of precatalysts ensures the efficient generation of the active catalytic species and allows one to accurately adjust the ligand:palladium ratio. The ligands, precatalysts and methodology developed in the Buchwald group are user friendly and have rendered previously difficult cross couplings reactions, much easier to achieve.

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