731013

Sigma-Aldrich

JackiePhos

95%

Synonym(s):
2-{Bis[3,5-bis(trifluoromethyl)phenyl]phosphino}-3,6-dimethoxy -2′,4′,6′-triisopropyl-1,1′-biphenyl, Bis(3,5-bis(trifluoromethyl)phenyl)(2′,4′,6′- triisopropyl-3,6-dimethoxybiphenyl-2-yl)phosphine
Empirical Formula (Hill Notation):
C39H37F12O2P
CAS Number:
Molecular Weight:
796.66
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

reaction suitability

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

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

mp

186-190 °C

functional group

phosphine

SMILES string

COc1ccc(OC)c(c1P(c2cc(cc(c2)C(F)(F)F)C(F)(F)F)c3cc(cc(c3)C(F)(F)F)C(F)(F)F)-c4c(cc(cc4C(C)C)C(C)C)C(C)C

InChI

1S/C39H37F12O2P/c1-19(2)22-11-29(20(3)4)33(30(12-22)21(5)6)34-31(52-7)9-10-32(53-8)35(34)54(27-15-23(36(40,41)42)13-24(16-27)37(43,44)45)28-17-25(38(46,47)48)14-26(18-28)39(49,50)51/h9-21H,1-8H3

InChI key

KYTUFIMHJNRPLC-UHFFFAOYSA-N

Application

Catalyst for N-Arylation reactions

Buchwald Phosphine Ligands for chemical Synthesis
JackiePhos is a Buchwald′s phosphine ligand which can be used for the:
  • glycosyl cross-coupling reaction of diaryliodonium triflates with anomeric stannanes to synthesize C-glycosides.
  • synthesis of gold-based catalyst complexes such as [Au(CH3CN)(JackiePhos)][SbF6] and [(JackiePhos)AuCl.
  • acylation of alkylcarbastannatranes.
  • synthesis of cyclic guanidines or cyclic ureas bearing dialkylaminomethyl groups in combination with Pd(acac)2 as a catalyst.

Packaging

1 g in glass bottle
100, 250 mg in glass bottle

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

Pd-Catalyzed Alkene Diamination Reactions of Nitrogen Electrophiles: Synthesis of Cyclic Guanidines and Ureas Bearing Dialkylaminomethyl Groups.
Peterson LJ, et al.
Organic Letters, 20(12), 3513-3517 (2018)
Gold-Catalyzed Intramolecular Regio-and Enantioselective Cycloisomerization of 1, 1-Bis (indolyl)-5-alkynes.
Huang L, et al.
Angewandte Chemie (International Edition in English), 125(26), 6899-6903 (2013)
Gold-Catalyzed Cyclization of 1-(Indol-3-yl)-3-alkyn-1-ols: Facile Synthesis of Diversified Carbazoles.
Zhang Z, et al.
Chemistry?A European Journal , 19(32), 10625-10631 (2013)
Stereospecific Palladium-Catalyzed Acylation of Enantioenriched Alkylcarbastannatranes: A General Alternative to Asymmetric Enolate Reactions.
Wang CY, et al.
Angewandte Chemie (International Edition in English), 56(3), 856-860 (2017)
Glycosyl Cross-Coupling with Diaryliodonium Salts: Access to Aryl C-Glycosides of Biomedical Relevance.
Yi D, et al.
Organic Letters, 20(7), 1936-1940 (2018)

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