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[1,1′-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II)

greener alternative

98%

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Synonym(s):
PdCl2(dtbpf)
Empirical Formula (Hill Notation):
C26H44Cl2FeP2Pd
CAS Number:
95408-45-0
Molecular Weight:
651.75
MDL number:
MFCD08064219
PubChem Substance ID:
329762308
NACRES:
NA.22

Assay

98%

form

powder

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

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

mp

203-208 °C

greener alternative category

Aligned

storage temp.

−20°C

SMILES string

[Fe].Cl[Pd]Cl.CC(C)(C)P([C]1[CH][CH][CH][CH]1)C(C)(C)C.CC(C)(C)P([C]2[CH][CH][CH][CH]2)C(C)(C)C

InChI

1S/2C13H22P.2ClH.Fe.Pd/c2*1-12(2,3)14(13(4,5)6)11-9-7-8-10-11;;;;/h2*7-10H,1-6H3;2*1H;;/q;;;;;+2/p-2

InChI key

JQZFOBWXNREQLO-UHFFFAOYSA-L

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General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Find details here.
[1,1′-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dtbpf)) participates as catalyst in Suzuki and Heck reactions. It is a preformed catalyst synthesized by a group of researchers at Johnson Matthey′s Catalysis and Chiral Technologies. It is an active catalyst for various Pd catalyzed cross-coupling reactions.
[1,1′-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) is an air-stable, highly active and versatile catalyst. It is an efficient catalyst for cross-coupling reactions. It participates as catalyst in various coupling reactions of the fine chemicals and pharmaceutical chemicals. It is commonly employed as homogeneous catalyst in the Suzuki reactions.

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
[1,1′-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dtbpf)) may be used as catalyst in the Suzuki cross-coupling reaction of various aromatic and heteroaromatic halides with methyliminodiacetic acid derivatives (MIDA boronates) at room temperature (in the absence of organic solvent). It may be employed as catalyst for the synthesis of chalcones, via cross-coupling reactions.
[1,1′-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) was used in the preparation of [PdCl2(bisphosphinometallocene)] complexes. These complexes are reported to be the catalyst precursors for the Buchwald-Hartwig reaction.
It is also employed as catalyst for greener Suzuki cross-coupling in TPGS-750-M.

On the Way Towards Greener Transition-Metal-Catalyzed Processes as Quantified by E Factors

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Bruce H Lipshutz et al.
Organic letters, 10(7), 1329-1332 (2008-03-14)
A nonionic amphiphile such as Triton X-100 or the vitamin E-based PTS, both of which form nanomicelles in water, promotes Heck cross-couplings of non-water-soluble partners at ambient temperatures. These are the first examples of Heck reactions conducted in water (as
An Effective Activation of Palladium Phosphine Complexes in Aqueous Phase Reactions of Hetero-Aromatic Boronic Acids with Aryl Halides.
Bumagin NA, et al.
Chemistry of Heterocyclic Compounds, 50(1), 19-25 (2011)
CRC International Symposium: Cross Coupling and Organometallics.
Colacot T.
Platinum Metals Rev., 52(3), 172-172 (2008)
A simple way of recycling of homogeneous catalyst in Suzuki reaction.
Manjunatha SG, et al.
Green Chemistry Letters and Reviews, 6(1), 77-87 (2013)
Synthesis and electrochemistry of late transition metal complexes containing 1, 1'-bis (dicyclohexylphosphino) ferrocene (dcpf). The X-ray structure of [PdCl 2 (dcpf)] and Buchwald-Hartwig catalysis using [PdCl2(bisphosphinometallocene)] precursors.
Hagopian LE, et al.
Journal of Organometallic Chemistry, 691(23), 4890-4900 (2006)
View All Related Papers

Articles

Procedures for Transition-Metal-Catalyzed Cross-Coupling Reactions in Water at Room Temperature using TPGS-750-M

TPGS-750-M, a second generation surfactant, is useful for room temperature, palladium and ruthenium-catalyzed reactions in water. Reactions include the Heck reaction, Suzuki-Miyaura reaction, Sonogashira reaction, Buchwald-Hartwig amination reaction, Negishi reaction, and olefin metathesis.

Heck Reaction

The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes and aryl or vinyl halides (or triflates) to afford substituted alkenes.

Protocols

Suzuki-Miyaura Reaction in Water at Room Temperature using TPGS-750-M

TPGS-750-M, a second generation surfactant, may be used for Suzuki-Miyaura Reactions in Water at Room Temperature

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