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718750

Sigma-Aldrich

BrettPhos Pd G1, Methyl t-Butyl Ether Adduct

may contain up to 1 mole equivalent of MTBE, 97%

Synonyme(s) :

(BrettPhos) palladium(II) phenethylamine chloride, BrettPhos Palladacycle, BrettPhos precatalyst, Chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,4′, 6′-triisopropyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II)

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About This Item

Formule empirique (notation de Hill):
C43H63ClNO2PPd
Poids moléculaire :
798.81
Code UNSPSC :
12161600
ID de substance PubChem :
329763603
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Pureté

97%

Forme

solid

Caractéristiques

generation 1

Pertinence de la réaction

core: palladium
reagent type: catalyst
reaction type: Cross Couplings

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

Pf

198-204 °C

Groupe fonctionnel

phosphine

Chaîne SMILES 

COC(C)(C)C.NCCc1ccccc1[Pd]Cl.COc2ccc(OC)c(c2P(C3CCCCC3)C4CCCCC4)-c5c(cc(cc5C(C)C)C(C)C)C(C)C

InChI

1S/C35H53O2P.C8H10N.C5H12O.ClH.Pd/c1-23(2)26-21-29(24(3)4)33(30(22-26)25(5)6)34-31(36-7)19-20-32(37-8)35(34)38(27-15-11-9-12-16-27)28-17-13-10-14-18-28;9-7-6-8-4-2-1-3-5-8;1-5(2,3)6-4;;/h19-25,27-28H,9-18H2,1-8H3;1-4H,6-7,9H2;1-4H3;1H;/q;;;;+1/p-1

Clé InChI

OWHWOTGYDWMPCA-UHFFFAOYSA-M

Description générale

BrettPhos Pd G1 is a Buchwald first generation (G1) palladacycle precatalyst that can be used in cross-coupling reactions for the formation of C-C, C–N, C–O, C–F, C–CF3, and C–S bonds. The formation of the active Pd(0) species in the G1 precatalyst is easy to generate, requiring merely a deprotonation with a base. The resulting catalyst is very active, even at temperatures down to −40 °C, and can be used in a variety of cross-coupling protocols.

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Catalyst for:
  • C,N-cross coupling of unprotected 3-halo-2-aminopyridines with primary and secondary amines
  • Amination reaction
  • N-arylation of aminophenols

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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

Contenu apparenté

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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