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936693

Sigma-Aldrich

tBuXPhos ChemBeads

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Synonym(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

Empirical Formula (Hill Notation):
C29H45P
CAS Number:
564483-19-8
Molecular Weight:
424.64
MDL number:
MFCD06411306
UNSPSC Code:
12352100

Quality Level

100

form

solid

composition

, 4-6 wt. % (loading)

reaction suitability

reagent type: ligand

SMILES string

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

InChI key

SACNIGZYDTUHKB-UHFFFAOYSA-N

General description

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)

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638080

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901904

tBuXPhos, 95%

924377

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928364

XPhos ChemBeads

931055

tBuXPhos Pd G3 ChemBeads

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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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.
Zhi-Ming Su et al.
ACS central science, 9(2), 159-165 (2023-02-28)
Lignin-derived aromatic chemicals offer a compelling alternative to petrochemical feedstocks, and new applications are the focus of extensive interest. 4-Hydroxybenzoic acid (H), vanillic acid (G), and syringic acid (S) are readily obtained via oxidative depolymerization of hardwood lignin substrates. Here
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
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