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763403

Sigma-Aldrich

RuPhos Pd G3

98%

Synonym(s):
(2-Dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate, RuPhos-Pd-G3, RuPhos-G3-Palladacycle
Empirical Formula (Hill Notation):
C43H56NO5PPdS
CAS Number:
Molecular Weight:
836.37
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

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

188-196 °C (decomposition)

functional group

phosphine

SMILES string

CS(=O)(=O)O[Pd]c1ccccc1-c2ccccc2N.CC(C)Oc3cccc(OC(C)C)c3-c4ccccc4P(C5CCCCC5)C6CCCCC6

InChI

1S/C30H43O2P.C12H10N.CH4O3S.Pd/c1-22(2)31-27-19-13-20-28(32-23(3)4)30(27)26-18-11-12-21-29(26)33(24-14-7-5-8-15-24)25-16-9-6-10-17-25;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h11-13,18-25H,5-10,14-17H2,1-4H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1

InChI key

AXZLIMCJMPNFFU-UHFFFAOYSA-M

General description

RuPhos Pd G3 is a third generation (G3) Buchwald precatalyst that can be used in cross-coupling reactions for the formation of C-C, C–N, C–O, C–F, C–CF3, and C–S bonds. It is air-, moisture-, and thermally-stable and is highly soluble in a wide range of common organic solvents. 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

RuPhos Pd G3 can be used as a pre-catalyst in the following protocols:
  • Palladium-catalyzed Suzuki coupling of 5-p-toluenesulfonyltetrazoles with arylboronic acids to synthesize 1,5-disubstituted tetrazoles.
  • Suzuki-Miyaura catalyst-transfer polycondensation (SCTP) of 3-alkylthiophenes in the presence of N-methylimidodiacetic (MIDA)-boronate monomers.
  • Suzuki-Miyaura-cross-coupling of aminothiophenes.

Packaging

250 mg in glass bottle
1, 5 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Aquatic Chronic 3 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

3-Cyanoallyl boronates are versatile building blocks in the synthesis of polysubstituted thiophenes.
Shao W, et al.
Chemical Science, 8(6), 4431-4436 (2017)
A Rational Design of Highly Controlled Suzuki-Miyaura Catalyst-Transfer Polycondensation for Precision Synthesis of Polythiophenes and their Block Copolymers: Marriage of Palladacycle Precatalysts with MIDA-boronates.
Seo KB, et al.
Journal of the American Chemical Society (2018)
Preparation of highly functionalized 1, 5-disubstituted tetrazoles via palladium-catalyzed Suzuki coupling.
Hennessy EJ, et al.
Tetrahedron Letters, 58(17), 1709-1713 (2017)

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.

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