745979

tBuBrettPhos Pd G3

96%

• Synonym(s): tert-BuBrettPhos-Pd-G3, [(2-Di-tert-butylphosphino-3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate
• Empirical Formula (Hill Notation): C₄₄H₆₂NO₅PPdS
• CAS Number: 1536473-72-9
• Molecular Weight: 854.43
• MDL number: MFCD25976528
• UNSPSC Code: 12161600
• PubChem Substance ID: 329765730
• NACRES: NA.22

Properties

• Quality Level: 100
• assay: 96%
• 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: 119-131 °C
• functional group: phosphine
• SMILES string: COC1=CC=C(C(P(C(C)(C)C)C(C)(C)C)=C1C2=C(C=C(C=C2C(C)C)C(C)C)C(C)C)OC.NC3=C(C=CC=C3)C4=C(C=CC=C4)[Pd]OS(C)(=O)=O
• 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

Description

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.

For small scale and high throughput uses, product is also available as ChemBeads (928313)

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable