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763039

XantPhos Pd G3

Name: XantPhos Pd G3
Brand: ALDRICH

95%, solid

Synonym(s):

[(4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate

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About This Item

Empirical Formula (Hill Notation):

C₅₂H₄₅NO₄P₂PdS

CAS Number:

1445085-97-1

Molecular Weight:

948.35

UNSPSC Code:

12161600

PubChem Substance ID:

329767021

NACRES:

NA.22

MDL number:

MFCD22572675

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Properties

Product Name

XantPhos Pd G3, 95%

Quality Level

100

product line

Buchwald precatalyst Generation 3

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

164-167 °C (decomposition)

functional group

phosphine

SMILES string

CS(=O)(=O)O[Pd]c1ccccc1-c2ccccc2N.CC3(C)c4cccc(P(c5ccccc5)c6ccccc6)c4Oc7c(cccc37)P(c8ccccc8)c9ccccc9

InChI

1S/C39H32OP2.C12H10N.CH4O3S.Pd/c1-39(2)33-25-15-27-35(41(29-17-7-3-8-18-29)30-19-9-4-10-20-30)37(33)40-38-34(39)26-16-28-36(38)42(31-21-11-5-12-22-31)32-23-13-6-14-24-32;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h3-28H,1-2H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1

InChI key

AJVXPGQYAKUTGX-UHFFFAOYSA-M

Description

General description

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

Application

XantPhos Pd G3 may be used in the following processes:

Negishi cross-coupling reaction during the synthesis of palmerolides.
Aminocarbonylation of heteroaryl bromides with carbon monoxide (CO) in the presence of triethylamine.
Coupling between polyglycosyl thiols and aglycon halides by C-S bond formation.

For small scale and high throughput uses, product is also available as ChemBeads (932213)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Scale-Up Guide: Buchwald-Hartwig Amination Reaction

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A synthetic approach to palmerolides via Negishi cross coupling. The challenge of the C15-C16 bond formation.

Carrillo J, et al.

Tetrahedron Letters, 55(33), 4623-4627 (2014)

Stereoretentive Palladium-Catalyzed Arylation, Alkenylation, and Alkynylation of 1-Thiosugars and Thiols Using Aminobiphenyl Palladacycle Precatalyst at Room Temperature.

Bruneau A, et al.

Chemistry (Weinheim An Der Bergstrasse, Germany), 21(23), 8375-8379 (2015)

2-Aminobiphenyl Palladacycles: The ?Most Powerful? Precatalysts in C-C and C-Heteroatom Cross-Couplings.