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Merck

730998

tBuBrettPhos

97%, solid

Synonym(s):

t-Bu Brett Phos, t-BuBrett-Phos, tertButylBrettPhos, 2-(Di-tert-butylphosphino)-2′,4′,6′- triisopropyl-3,6-dimethoxy-1,1′-biphenyl, t-BuBrett Phos, t-BuBrettPhos, [3,6-Dimethoxy-2′,4′,6′-tris(1-methylethyl) [1,1′-biphenyl]-2-yl]bis(1,1-dimethylethyl)phosphine, tert-ButylBrettPhos

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About This Item

Empirical Formula (Hill Notation):
C31H49O2P
CAS Number:
Molecular Weight:
484.69
UNSPSC Code:
12352112
PubChem Substance ID:
NACRES:
NA.22
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Product Name

tBuBrettPhos, 97%

assay

97%

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: C-X Bond Formation, reagent type: ligand
reaction type: Fluorinations

mp

166-170 °C

functional group

phosphine

Quality Level

General description

tBuBrettPhos is a dialkylbiaryl phosphine ligand developed by the Buchwald group. It promotes cross-coupling reactions more efficiently and exhibits improved reactivity compared to other catalytic systems.

tBuBrettPhos is a phosphine ligand widely used in palladium-catalyzed cross-coupling reactions.

Application

Common applications
  • Buchwald-Hartwig amination and C-O coupling
  • Suzuki, Negishi, Stille, Hiyama, Sonogashira cross-couplings
  • α-Arylation reaction


New Applications:
  • Conversion of aryl and vinyl triflates to bromides and chlorides
  • Conversion of aryl triflates to aryl fluorides
  • O-Arylation of ethyl acetohydroximate
  • Conversion of aryl chlorides and sulfonates to nitroaromatics

Features and Benefits

  • White crystalline solid
  • Air- and moisture-stable
  • Thermally stable
  • Highly efficient
  • Wide functional group tolerance
  • Excellent selectivity and conversion

Legal Information

Usage subject to US Patent 7,858,784

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Pd-Catalyzed Conversion of Aryl Chlorides, Triflates, and Nonaflates to Nitroaromatics.
Fors BP, et al.
Journal of the American Chemical Society, 131, 12898-12898 (2009)
Transition-metal-catalyzed cross-couplings through carbene migratory insertion
Xia Y, et al.
Chemical Reviews, 117(23), 13810-13889 (2017)
Pd-Catalyzed O-Arylation of Ethyl Acetohydroximate: Synthesis of O-Arylhydroxylamines and Substituted Benzofuran
Maimone TJ, et al.
Journal of the American Chemical Society, 132, 9990-9990 (2010)
Formation of ArF from LPdAr (F): Catalytic conversion of aryl triflates to aryl fluorides.
Watson DA, et al.
Science, 325, 1661-1661 (2009)
Xiaoqiang Shen et al.
Journal of the American Chemical Society, 132(40), 14076-14078 (2010-09-23)
The palladium-catalyzed conversion of aryl and vinyl triflates to aryl and vinyl halides (bromides and chlorides) has been developed using dialkylbiaryl phosphine ligands. A variety of aryl, heteroaryl, and vinyl halides can be prepared via this method in good to

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