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804967

Sigma-Aldrich

rac-BINAP-Pd-G3

95%

Synonym(s):

[2′-(amino-κN)[1,1′-biphenyl]-2-yl-κC][[2′-(diphenylphosphino)[1,1′-binaphthalen]-2-yl]diphenylphosphine-κP](methanesulfonato-κO)- palladium 

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About This Item

Empirical Formula (Hill Notation):
C57H45NO3P2PdS
CAS Number:
2151915-22-7
Molecular Weight:
992.40
UNSPSC Code:
12161600
PubChem Substance ID:
329768912
NACRES:
NA.22

Quality Level

100

Assay

95%

form

solid

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

175-180 °C

functional group

phosphine

SMILES string

CS(O[Pd-2]1([P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=C(C5=C6C(C=CC=C6)=CC=C5P(C7=CC=CC=C7)C8=CC=CC=C8)C9=CC=CC=C9C=C4)C%10=C(C%11=C([NH2+]1)C=CC=C%11)C=CC=C%10)(=O)=O

InChI

1S/C44H32P2.C12H10N.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;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h1-32H;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1

InChI key

BVYJEOTVUJMCBM-UHFFFAOYSA-M

Related Categories

General description

rac-BINAP-Pd-G3 is a third generation (G3) Buchwald precatalyst. t is air, moisture and thermally-stable and is highly soluble in a wide range of common organic solvents. It has long life in solutions. rac-BINAP-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. It

Application

Pd precatalyst for cross-coupling

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN6588
SHBM2859
SHBL4569
SHBL0561
SHBJ3104

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Articles

Scale-Up Guide: Buchwald-Hartwig Amination Reaction

All of the preformed catalysts used in the kit are air and moisture stable complexes in their commercially available form. Once activated by base under the reaction conditions they become sensitive to air. To best enable scale-up success, the use of standard Schlenk technique is recommended.

KitAlysis™ C-N (Buchwald-Hartwig) High-Throughput Screening Kit

All contents in the foil bag are weighed, plated, packed, and sealed in a glove box under nitrogen.

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.

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