695874

Sigma-Aldrich

t-BuDavePhos

Synonym(s):
2-Di-tert-butylphosphino-2′-(N,N-dimethylamino)biphenyl, tBuDavePhos, t-Butyl DavePhos, 2′-(Di-tert-butylphosphino)-N,N-dimethylbiphenyl-2-amine
Empirical Formula (Hill Notation):
C22H32NP
CAS Number:
Molecular Weight:
341.47
MDL number:
PubChem Substance ID:
NACRES:
NA.22

reaction suitability

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

Quality Level

mp

114-118 °C

functional group

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

InChI key

PHLPNEHPCYZBNZ-UHFFFAOYSA-N

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

hazcat

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

Target Organs

Respiratory system

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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