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Key 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)

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About This Item

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

form

powder

Quality Level

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)

Articles

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.

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