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903701

Sigma-Aldrich

tBuDavePhos Pd G3

1:1 THF adduct

Synonym(s):

t-BuDavePhos G3 Palladacycle, t-BuDavePhos Palladacycle

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About This Item

Linear Formula:
C35H45N2O3PPdS · C4H8O
UNSPSC Code:
12161600
NACRES:
NA.22

form

powder or crystals

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

functional group

phosphine

SMILES string

CN(C1=C(C2=C(P(C(C)(C)C)C(C)(C)C)C=CC=C2)C=CC=C1)C.NC3=C(C4=C([Pd]OS(C)(=O)=O)C=CC=C4)C=CC=C3.C5COCC5

Related Categories

General description

tBuDavePhos 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 a long life in solutions. tBuDavePhos 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

tBuDavePhos Pd G3 has been used as a precatalyst for the Synthesis of Aryl Sulfonamides via Palladium-Catalyzed Chlorosulfonylation of Arylboronic Acids. It may also be used for a variety of C-C and C-N cross-coupling reactions.

Other Notes

Technology Spotlight: G3 and G4 Buchwald Precatalysts

Synthesis of Aryl Sulfonamides via Palladium-Catalyzed Chlorosulfonylation of Arylboronic Acids

Design and preparation of new palladium precatalysts for C-C and C-N cross-coupling reactions

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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J Robb DeBergh et al.
Journal of the American Chemical Society, 135(29), 10638-10641 (2013-07-11)
A palladium-catalyzed method for the preparation of sulfonamides is described. The process exhibits significant functional group tolerance and allows for the preparation of a number of arylsulfonyl chlorides and sulfonamides under mild conditions.
Nicholas C Bruno et al.
Chemical science, 4, 916-920 (2013-05-15)
A series of easily prepared, phosphine-ligated palladium precatalysts based on the 2-aminobiphenyl scaffold have been prepared. The role of the precatalyst-associated labile halide (or pseudohalide) in the formation and stability of the palladacycle has been examined. It was found that

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