730998

Sigma-Aldrich

tBuBrettPhos

97%

Synonym(s):
2-(Di-tert-butylphosphino)-2′,4′,6′- triisopropyl-3,6-dimethoxy-1,1′-biphenyl, t-BuBrettPhos, tertButylBrettPhos, t-BuBrett-Phos, t-Bu Brett Phos, t-BuBrett Phos, tert-ButylBrettPhos, [3,6-Dimethoxy-2′,4′,6′-tris(1-methylethyl) [1,1′-biphenyl]-2-yl]bis(1,1-dimethylethyl)phosphine
Empirical Formula (Hill Notation):
C31H49O2P
CAS Number:
Molecular Weight:
484.69
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

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

SMILES string

COc1ccc(OC)c(c1P(C(C)(C)C)C(C)(C)C)-c2c(cc(cc2C(C)C)C(C)C)C(C)C

InChI

1S/C31H49O2P/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/h15-21H,1-14H3

InChI key

REWLCYPYZCHYSS-UHFFFAOYSA-N

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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.

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

Packaging

1, 5, 50 g in glass bottle
100, 500 mg in glass bottle

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_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Formation of ArF from LPdAr (F): Catalytic conversion of aryl triflates to aryl fluorides.
Watson DA, et al.
Science, 325, 1661-1661 (2009)
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)
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)
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...
David S Surry et al.
Chemical science, 2(1), 27-50 (2011-01-01)
Dialkylbiaryl phosphines are a valuable class of ligand for Pd-catalyzed amination reactions and have been applied in a range of contexts. This review attempts to aid the reader in the selection of the best choice of reaction conditions and ligand...

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