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708739

Sigma-Aldrich

Chloro-[2-(di-tert.-butylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl][2-(2-aminoethyl)-phenyl)]-palladium(II)

Synonym(e):

t-BuXPhos-palladium(II)-phenylethylaminchlorid, [2-(Di-tert.-butylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl][2-(2-aminoethyl)-phenyl)]-palladium(II)-chlorid

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About This Item

Empirische Formel (Hill-System):
C37H55ClNPPd
CAS-Nummer:
1142811-12-8
Molekulargewicht:
686.69
MDL-Nummer:
MFCD12911909
UNSPSC-Code:
12161600
PubChem Substanz-ID:
329762821
NACRES:
NA.22

Form

solid

Leistungsmerkmale

generation 1

Eignung der Reaktion

core: palladium
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: catalyst
reaction type: Cross Couplings

mp (Schmelzpunkt)

150-159 °C

Funktionelle Gruppe

phosphine

SMILES String

NCCc1ccccc1[Pd]Cl.CC(C)c2cc(C(C)C)c(c(c2)C(C)C)-c3ccccc3P(C(C)(C)C)C(C)(C)C

InChI

1S/C29H45P.C8H10N.ClH.Pd/c1-19(2)22-17-24(20(3)4)27(25(18-22)21(5)6)23-15-13-14-16-26(23)30(28(7,8)9)29(10,11)12;9-7-6-8-4-2-1-3-5-8;;/h13-21H,1-12H3;1-4H,6-7,9H2;1H;/q;;;+1/p-1

InChIKey

LQRWNWRVOIDQOD-UHFFFAOYSA-M

Anwendung

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
Catalyst for C-C bond and C-N bond formation.

Rechtliche Hinweise

Usage subject to US Patents 6307087 and 6395916.

Piktogramme

Health hazardExclamation mark
GHS08,GHS07

Signalwort

Warning

Gefahreneinstufungen

Carc. 2 - 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

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Brian K Lee et al.
Tetrahedron letters, 50(26), 3672-3674 (2009-07-01)
Simple and efficient procedures for the Pd-catalyzed cross-coupling reaction of aryl chlorides and dimethylamine are described. At room temperature with a strong base, t-BuXPhos is employed as the supporting ligand; at 110 °C with a weak base, XPhos is employed
Mark R Biscoe et al.
Organic letters, 11(8), 1773-1775 (2009-03-20)
Simple, efficient procedures for the monoarylation of acetate esters and aryl methyl ketones using aryl chlorides are presented. Previously, no general method was available to ensure the highly selective monoarylation of these classes of substrates using aryl chlorides. Using palladium
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

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