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Sigma-Aldrich

tBuXPhos

greener alternative

98%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C29H45P
CAS Number:
Molecular Weight:
424.64
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

form

solid

reaction suitability

reaction type: Cross Couplings
reagent type: ligand
reaction type: Arylations

reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction

reagent type: ligand
reaction type: Carboxylations

reagent type: ligand
reaction type: Decarboxylations

greener alternative product score

old score: 12
new score: 1
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greener alternative product characteristics

Atom Economy
Design for Energy Efficiency
Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

148-151 °C (lit.)

functional group

phosphine

greener alternative category

SMILES string

CC(C)c1cc(C(C)C)c(c(c1)C(C)C)-c2ccccc2P(C(C)(C)C)C(C)(C)C

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

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General description

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.
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Learn more about Buchwald Phosphine Ligands

Application

tBuXPhos has been used in the preparation of [tBuXPhosAu(MeCN)]BAr4F, a gold catalyst for the intermolecular [2+2] cycloaddition of terminal arylalkynes with substituted alkenes to form functionalized cyclobutenes with high regioselectivity.
tBuXPhos is a ligand for Pd-catalyzed C-O and C-N bond formation.
It can be used in the following reactions:
  • Palladium-catalyzed Tsuji-Trost substitution and cross-coupling of benzylic fluorides.
  • Palladium-catalyzed C-N cross-coupling of sulfinamides and aryl halides.
  • Palladium-catalyzed rapid methoxylation and deuteriomethoxylation of bromo-chalcones.

Legal Information

Usage subject to Patents: EP 1097158; JP 5758844; CA 2336691

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Description
Pricing

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

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Palladium-catalyzed substitution and cross-coupling of benzylic fluorides.
Blessley G, et al.
Organic Letters, 14(11), 2754-2757 (2012)
Arkaitz Correa et al.
Journal of the American Chemical Society, 131(44), 15974-15975 (2009-11-06)
A novel protocol for the direct carbon dioxide insertion (CO(2)) into aryl halides in a catalytic manner is presented herein. Unlike other carboxylation methods using CO(2), there is no need for the synthesis of the corresponding organometallic intermediates. Additionally, and
Intermolecular [2+ 2] Cycloaddition of Alkynes with Alkenes Catalyzed by Gold (I).
de Orbe ME and Echavarren AM.
Organic Syntheses, 93, 115-126 (2016)
Palladium?Catalyzed Rapid Methoxylation and Deuteriomethoxylation of Bromo?chalcones: Uncovering the Catalytic Activity of the Pd/tBuXPhos Catalyst System.
Rangarajan T M, et al.
ChemistrySelect, 1(21), 6894-6901 (2016)
Palladium-Catalyzed C?N Cross Coupling of Sulfinamides and Aryl Halides.
Sun X, et al.
The Journal of Organic Chemistry, 77(9), 4454-4459 (2012)

Articles

Buchwald Phosphine Ligands

Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.

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