All Photos(2)

745979

Sigma-Aldrich

tBuBrettPhos Pd G3

96%

Synonym(s):
[(2-Di-tert-butylphosphino-3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate, tert-BuBrettPhos-Pd-G3
Empirical Formula (Hill Notation):
C44H62NO5PPdS
CAS Number:
Molecular Weight:
854.43
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

96%

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

119-131 °C

functional group

phosphine

SMILES string

COC1=CC=C(OC)C(P(C(C)(C)C)C(C)(C)C)=C1C2=C(C(C)C)C=C(C(C)C)C=C2C(C)C.NC3=C(C4=C([Pd]OS(C)(=O)=O)C=CC=C4)C=CC=C3

InChI

1S/C31H49O2P.C12H10N.CH4O3S.Pd/c1-19(2)22-17-23(20(3)4)27(24(18-22)21(5)6)28-25(32-13)15-16-26(33-14)29(28)34(30(7,8)9)31(10,11)12;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h15-21H,1-14H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1

InChI key

GAQPAUHHECNHNS-UHFFFAOYSA-M

General description

tBuBrettPhos 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

tBuBrettPhos Pd G3 has been used as a precatalyst for the N-arylation of amino acid esters with aryl triflates under mild reaction conditions and minimal racemization of the amino acid ester. It may also be used to catalyze the conversion of aryl halides to phenols in the presence of benzaldoxime as a hydroxide surrogate.

Packaging

1, 2, 5 g in glass bottle
100, 500 mg in glass bottle

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Synthesis of Complex Phenols Enabled by a Rationally Designed Hydroxide Surrogate.
Fier PS & Maloney KM
Angewandte Chemie (International Edition in English), 56(16), 4478-4482 (2017)
Hailey A Young et al.
The Journal of organic chemistry, 85(3), 1748-1755 (2019-12-04)
Palladium-catalyzed N-arylations of amino acid tert-butyl esters using 4-bromo-N,N-dimethylaniline as a coupling partner are reported. The resulting N-aryl amino acid esters are suitable building blocks for the synthesis of electron-rich N-aryl peptides, which undergo oxidative couplings to aminooxy groups to...
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)...

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