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936693

Sigma-Aldrich

tBuXPhos ChemBeads

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Synonyme(s) :

2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl ChemBeads, tert-Butyl Xphos ChemBeads, t-Bu Xphos ChemBeads, tBuXPhos

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About This Item

Formule empirique (notation de Hill):
C29H45P
Numéro CAS:
564483-19-8
Poids moléculaire :
424.64
Numéro MDL:
MFCD06411306
Code UNSPSC :
12352100

Niveau de qualité

100

Forme

solid

Composition

, 4-6 wt. % (loading)

Pertinence de la réaction

reagent type: ligand

Chaîne SMILES 

CC(C)(C)P(C(C)(C)C)C1=C(C2=C(C(C)C)C=C(C(C)C)C=C2C(C)C)C=CC=C1

InChI

InChI=1S/C29H45P/c1-19(2)22-17-24(20(3)4)27(25(18-22)21(5)6)23-15-13-14-16-26(23)30(28(7,8)9)29(10,11)12/h13-21H,1-12H3

Clé InChI

SACNIGZYDTUHKB-UHFFFAOYSA-N

Description générale

The ChemBeads product of tBuXPhos [2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl] is an air-stable, electron-rich biaryl phosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions. Loaded on glass beads for use in high-throughput expermentation (HTE).

Application

tBuXPhos has been used as a ligand in many C-N and C-O bond forming reactions, as well many others including:
- The palladium-catalyzed Tsuji-Trost substitution and cross-coupling of benzylic fluorides.
- The palladium-catalyzed C-N cross-coupling of sulfinamides and aryl halides.
- The protoboration of alkynes.
- ArF-alkynyl coupling with fluorinated aryls.
- The Ni & Ni/Pd reductive coupling of lignan-derived aromatics to biobased platicizers.
- The palladium-catalyzed fluorination of cyclic vinyl triflates.
ChemBeads are chemical coated glass beads. ChemBeads offer improved flowability and chemical uniformity perfect for automated solid dispensing and high-throughput experimentation. The method of creating ChemBeads uses no other chemicals or surfactants allowing the user to accurately dispense sub-milligram amounts of chemical.
For general uses, product is also available in powdered form (638080)

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

638080

tBuXPhos, 98%

901904

tBuXPhos, 95%

924377

Palladium(II) Acetate ChemBeads

928364

XPhos ChemBeads

931055

tBuXPhos Pd G3 ChemBeads

Code de la classe de stockage

13 - Non Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Lot/Batch Number

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Consulter la Bibliothèque de documents

Xiaofei Sun et al.
The Journal of organic chemistry, 77(9), 4454-4459 (2012-03-31)
The palladium-catalyzed C-N cross coupling of sulfinamides and aryl halides is reported. In the presence of Pd(2)(dba)(3), tBuXPhos, NaOH, and a small amount of water, the C-N cross coupling of chiral tert-butanesulfinamide and aryl halides was accomplished to give N-aryl
Lei Xu et al.
The Journal of organic chemistry, 87(21), 14879-14888 (2022-10-13)
The versions of Miyaura borylation and protoboration of alkynes catalyzed by low loadings of palladium (400 mol ppm = 0.04 mol %) have been developed. These transformations have a broad substrate scope, good functional-group compatibility, and gram-scale synthetic ability.
Palladium-catalyzed substitution and cross-coupling of benzylic fluorides
Blessley G, et al.
Organic Letters, 14(11), 2754-2757 (2012)
Yuxuan Ye et al.
Angewandte Chemie (International ed. in English), 62(15), e202300109-e202300109 (2023-02-13)
Pd-catalyzed nucleophilic fluorination reactions are important methods for the synthesis of fluoroarenes and fluoroalkenes. However, these reactions can generate a mixture of regioisomeric products that are often difficult to separate. While investigating the Pd-catalyzed fluorination of cyclic vinyl triflates, we
Palladium-catalyzed substitution and cross-coupling of benzylic fluorides
Blessley G, et al.
Organic Letters, 14(11), 2754-2757 (2012)
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