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Merck

695874

Sigma-Aldrich

2-Di-tert.-butylphosphino-2′-(N,N-dimethylamino)-biphenyl

Synonym(e):

tBu-DavePhos

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About This Item

Empirische Formel (Hill-System):
C22H32NP
CAS-Nummer:
Molekulargewicht:
341.47
MDL-Nummer:
UNSPSC-Code:
12352116
PubChem Substanz-ID:
NACRES:
NA.22

Form

solid

Qualitätsniveau

Eignung der Reaktion

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

mp (Schmelzpunkt)

114-118 °C

Funktionelle Gruppe

phosphine

SMILES String

CN(C)c1ccccc1-c2ccccc2P(C(C)(C)C)C(C)(C)C

InChI

1S/C22H32NP/c1-21(2,3)24(22(4,5)6)20-16-12-10-14-18(20)17-13-9-11-15-19(17)23(7)8/h9-16H,1-8H3

InChIKey

PHLPNEHPCYZBNZ-UHFFFAOYSA-N

Anwendung

Learn more about Buchwald Phosphine Ligands

Dialkylbiaryl phosphine ligand often used for Pd-catalyzed reactions in a range of contexts.

Piktogramme

Exclamation mark

Signalwort

Warning

Gefahreneinstufungen

Aquatic Chronic 4 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves


Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

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
Ruben Martin et al.
Accounts of chemical research, 41(11), 1461-1473 (2008-07-16)
The cores of many types of polymers, ligands, natural products, and pharmaceuticals contain biaryl or substituted aromatic structures, and efficient methods of synthesizing these structures are crucial to the work of a broad spectrum of organic chemists. Recently, Pd-catalyzed carbon-carbon
David S Surry et al.
Angewandte Chemie (International ed. in English), 47(34), 6338-6361 (2008-07-30)
Palladium-catalyzed amination reactions of aryl halides have undergone rapid development in the last 12 years, largely driven by the implementation of new classes of ligands. Biaryl phosphanes have proven to provide especially active catalysts in this context. This Review discusses

Artikel

Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.

Verwandter Inhalt

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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