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[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane

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Synonym(s):
Pd(dppf)Cl2 · CH2Cl2, Pd(dppf)Cl2 · DCM, [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1:1)
Empirical Formula (Hill Notation):
C35H30Cl4FeP2Pd
CAS Number:
Molecular Weight:
816.64
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

solid

Quality Level

reaction suitability

core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Cross Couplings
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

mp

275-280 °C

SMILES string

[Fe].ClCCl.Cl[Pd]Cl.[CH]1[CH][CH][C]([CH]1)P(c2ccccc2)c3ccccc3.[CH]4[CH][CH][C]([CH]4)P(c5ccccc5)c6ccccc6

InChI

1S/2C17H14P.CH2Cl2.2ClH.Fe.Pd/c2*1-3-9-15(10-4-1)18(17-13-7-8-14-17)16-11-5-2-6-12-16;2-1-3;;;;/h2*1-14H;1H2;2*1H;;/q;;;;;;+2/p-2

InChI key

CWHRHCATIKFSND-UHFFFAOYSA-L

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This Item
697230345237713929
Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

-

reaction suitability

core: palladium, reaction type: Cross Couplings, reaction type: Hiyama Coupling, reaction type: Sonogashira Coupling, reaction type: Suzuki-Miyaura Coupling, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Negishi Coupling, reagent type: catalyst, reaction type: Heck Reaction, reaction type: Stille Coupling

reaction suitability

core: palladium, reaction type: Cross Couplings, 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: Buchwald-Hartwig Cross Coupling Reaction

reaction suitability

-

reaction suitability

-

mp

275-280 °C

mp

266-283 °C (lit.)

mp

-

mp

-

Analysis Note

Catalyst employed in the borylation of aryl halides with Bis(pinacolato)diboron(473294) as well as the coupling of the derived arylboronic esters with aryl halides leading to biaryls. Also used in the synthesis of lactams by CO insertion and medium-ring aryl ethers by intramolecular coupling of an aryl halide with an alcohol.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Tetrahedron, 62, 2006-2006 (2006)
Songnian Lin et al.
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A full account of the total syntheses of proteasome inhibitors TMC-95A and -B is provided. A key feature of the syntheses involved installation of a cis-propenylamide moiety by a thermal rearrangement of an alpha-silylallyl amide. The scope and mechanism of
Barry M Trost et al.
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An asymmetric synthesis of the benzazocine core of FR900482 has been achieved in 15 steps from 3,5-dinitro-p-toluic acid. Key features of the synthesis include an enantioselective N-methylephedrine-mediated zinc acetylide addition to a highly enolizable arylacetaldehyde and a novel Pd-catalyzed carbonylative
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