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Key Documents

799718

Sigma-Aldrich

AlPhos

Synonyme(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

Formule empirique (notation de Hill):
C52H67F4OP
Numéro CAS:
Poids moléculaire :
815.06
Code UNSPSC :
12161600
ID de substance PubChem :
Nomenclature NACRES :
NA.22

Pureté

≥95%

Niveau de qualité

Forme

powder

Capacité de réaction

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

Pertinence de la réaction

reagent type: ligand
reaction type: Cross Couplings

Pf

218-223 °C

Groupe fonctionnel

phosphine

Température de stockage

−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?

Clé InChI

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3


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Organometallics, 34(19), 4775-4780 (2015)
A fluorinated ligand enables room-temperature and regioselective Pd-catalyzed fluorination of aryl triflates and bromides
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Journal of the American Chemical Society, 137(41), 13433-13438 (2015)
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Israel Journal of Chemistry, 60(3-4), 180-194 (2020)

Articles

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Contenu apparenté

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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