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753246

Sigma-Aldrich

RuPhos Pd G2

Synonym(s):

2nd Generation RuPhos Precatalyst, Chloro(2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II), RuPhos-Pd-G2

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About This Item

Empirical Formula (Hill Notation):
C42H53ClNO2PPd
CAS Number:
1375325-68-0
Molecular Weight:
776.72
MDL number:
MFCD20264899
UNSPSC Code:
12161600
PubChem Substance ID:
329766346
NACRES:
NA.22

form

solid

feature

generation 2

reaction suitability

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

195-197 °C

functional group

phosphine

SMILES string

Nc1ccccc1-c2ccccc2[Pd]Cl.CC(C)Oc3cccc(OC(C)C)c3-c4ccccc4P(C5CCCCC5)C6CCCCC6

InChI

1S/C30H43O2P.C12H10N.ClH.Pd/c1-22(2)31-27-19-13-20-28(32-23(3)4)30(27)26-18-11-12-21-29(26)33(24-14-7-5-8-15-24)25-16-9-6-10-17-25;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;;/h11-13,18-25H,5-10,14-17H2,1-4H3;1-6,8-9H,13H2;1H;/q;;;+1/p-1

InChI key

VPDRBFBKNSFRSS-UHFFFAOYSA-M

General description

RuPhos Pd G2 is a second generation (G2) precatalyst containing a biphenyl-based ligand. Product participates in various palladium catalyzed cross-coupling reactions, C-C, C-N, and C-O bond formation reactions and Suzuki-Miyaura coupling reactions. It generates active Pd catalyst at room temperature in the presence of weak phosphate or carbonate bases.

Application

RuPhos Pd G2 may be employed as precatalyst in the preparation of fluoro-substituted diazatetracenes and diazapentacenes, via Pd-catalyzed aryl amination reaction.

Other Notes

May contain <1% acetone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Jonas Schwaben et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 21(39), 13758-13771 (2015-08-08)
Non-symmetrical 6,13-disubstituted pentacenes bearing trifluoromethyl and aryl substituents have been synthesized starting from pentacenequinone. Diazapentacenes with a variety of fluorine substituents were prepared either via a Hartwig-Buchwald aryl amination route or by a SNAr strategy. As a result of a

Articles

Scale-Up Guide: Buchwald-Hartwig Amination Reaction

All of the preformed catalysts used in the kit are air and moisture stable complexes in their commercially available form. Once activated by base under the reaction conditions they become sensitive to air. To best enable scale-up success, the use of standard Schlenk technique is recommended.

KitAlysis™ C-N (Buchwald-Hartwig) High-Throughput Screening Kit

All contents in the foil bag are weighed, plated, packed, and sealed in a glove box under nitrogen.

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