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Sigma-Aldrich

AlPhos

Synonym(s):

Di-1-adamantyl(4″-butyl-2″,3″,5″,6″-tetrafluoro-2′,4′,6′-triisopropyl-2-methoxy-meta-terphenyl)phosphine

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About This Item

Empirical Formula (Hill Notation):
C52H67F4OP
CAS Number:
1805783-60-1
Molecular Weight:
815.06
UNSPSC Code:
12161600
PubChem Substance ID:
329768101
NACRES:
NA.22

Assay

≥95%

Quality Level

100

form

powder

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand
reaction type: Cross Couplings

mp

218-223 °C

functional group

phosphine

storage temp.

−20°C

InChI

1S/C52H67F4OP/c1-9-10-12-38-46(53)48(55)45(49(56)47(38)54)44-40(29(4)5)21-39(28(2)3)43(42(44)30(6)7)37-13-11-14-41(57-8)50(37)58(51-22-31-15-32(23-51)17-33(16-31)24-51)52-25-34-18-35(26-52)20-36(19-34)27-52/h11,13-14,21,28-36H,9-10,12,15-20,22-27H2,1-8H3/t31-,32+,33?,34-,35+,36?,51+,52?,58?

InChI key

ALWIRDZSIXWCBO-VABCSHEKSA-N

Application

AlPhos is a biaryl monophosphine ligand that can be used:
  • In the Pd-catalyzed Buchwald-Hartwig cross-coupling reactions.
  • To synthesize highly regioselective aryl fluorides by Pd-catalyzed fluorination of a variety of activated aryl and heteroaryl triflates and bromides.
  • To prepare aryl thioethers by C–S cross-coupling of thiols with aromatic electrophile in the presence of palladium catalyst.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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Monophosphine Ligands Promote Pd-Catalyzed C-S Cross-Coupling Reactions at Room Temperature with Soluble Bases
Xu Jessica, et al.
ACS Catalysis, 9(7), 6461-6466 (2019)
A fluorinated ligand enables room-temperature and regioselective Pd-catalyzed fluorination of aryl triflates and bromides
Sather AC, et al.
Journal of the American Chemical Society, 137(41), 13433-13438 (2015)
In-depth assessment of the palladium-catalyzed fluorination of five-membered heteroaryl bromides
Milner PJ, et al.
Organometallics, 34(19), 4775-4780 (2015)

Articles

AlPhos and [(AlPhosPd)2•COD] for Pd-Catalyzed Fluorination

Fluorine containing aromatics (ArF) are desirable compounds with applications in medicinal chemistry and the agricultural industry.

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Buchwald Group – Professor Product Portal

The Buchwald group has developed a series of highly active and versatile palladium precatalysts and biarylphosphine ligands used in cross-coupling reactions for the formation of C-C, C–N, C–O, C–F, C–CF3, and C–S bonds. The ligands are electron-rich, and highly tunable to provide catalyst systems with a diverse scope, high stability and reactivity. Furthermore, the new series of precatalysts are air-, moisture and thermally-stable and display good solubility in common organic solvents. The use of precatalysts ensures the efficient generation of the active catalytic species and allows one to accurately adjust the ligand:palladium ratio. The ligands, precatalysts and methodology developed in the Buchwald group are user friendly and have rendered previously difficult cross couplings reactions, much easier to achieve.

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