Skip to Content
MilliporeSigma
All Photos(2)

Documents

900340

Sigma-Aldrich

rac-BINAP Pd G4

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(2)

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)

Articles

G3 and G4 Buchwald Precatalysts

G3 and G4 Buchwald palladium precatalysts are the newest air, moisture, and thermally stable crossing-coupling complexes used in bond formation for their versatility and high reactivity.

Related Content

Buchwald Group – Professor Product Portal

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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service