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936669

Sigma-Aldrich

DPPF ChemBeads

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Synonym(s):

DPPF, 1,1′-Bis(diphenylphosphino)ferrocene ChemBeads, 1,1′-Ferrocenediyl-bis(diphenylphosphine) ChemBeads, 1,1′-Ferrocenediyl-bis(diphenylphosphine), dppf

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About This Item

Empirical Formula (Hill Notation):
C34H28FeP2
CAS Number:
12150-46-8
Molecular Weight:
554.38
MDL number:
MFCD00001422
UNSPSC Code:
12352100

form

solid

Quality Level

100

composition

loading, 4-6 wt. %

mp

181-182 °C (dec.) (lit.)

SMILES string

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

InChI

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

InChI key

HPXNTHKXCYMIJL-UHFFFAOYSA-N

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General description

The ChemBeads product of the 1,1′-Bis(diphenylphosphino)ferrocene (DPPF) ligand. DPPF is a bis-phosphine ligand bearing two diphenylphosphine moieties with a ferrocene backbone. Loaded on glass beads for use in high-throughput expermentation (HTE).

Application

  • DPPF has been used as a ligand in:
  • The ruthenium catalyzed N-alkylation of amines and sulfonamides using borrowing hydrogen methodology.[1] (19191700)
  • The cooperative Cu/Pd catalyzed borylallenylation of trifluoromethyl-1,3-enynes to generate conjugated bisallenes.[2] (36321461)
  • The cooperative Cu/Pd catlyzed borocarbonylation of ethylene.[3] (36226440)
  • The gold catalyzed synthesis of 2-phosphoryl indolin-3-ones.[4] (35815915)
  • The iron-catalyzed vinylzincation of terminal alkynes.[5] (34935372) ChemBeads are chemical coated glass beads. ChemBeads offer improved flowability and chemical uniformity perfect for automated solid dispensing and high-throughput experimentation. The method of creating ChemBeads uses no other chemicals or surfactants allowing the user to accurately dispense sub-milligram amounts of chemical.
  • For general uses, product is also available in powdered form (177261)

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Shang-Hai Yu et al.
Chemical communications (Cambridge, England), 58(92), 12871-12874 (2022-11-03)
A cooperative Cu/Pd-catalysed borylallenylation of 2-trifluoromethyl-1,3-enynes with propargylic carbonates under mild reaction conditions was developed. This method provides facile and efficient access to conjugated bisallenes with a broad range of functional groups. Both aromatic and aliphatic 1,3-enynes can be utilized
Qiang Huang et al.
Journal of the American Chemical Society, 144(1), 515-526 (2021-12-23)
Organozinc reagents are among the most commonly used organometallic reagents in modern synthetic chemistry, and multifunctionalized organozinc reagents can be synthesized from structurally simple, readily available ones by means of alkyne carbozincation. However, this method suffers from poor tolerance for
M Haniti S A Hamid et al.
Journal of the American Chemical Society, 131(5), 1766-1774 (2009-02-05)
The alkylation of amines by alcohols has been achieved using 0.5 mol % [Ru(p-cymene)Cl(2)](2) with the bidentate phosphines dppf or DPEphos as the catalyst. Primary amines have been converted into secondary amines, and secondary amines into tertiary amines, including the
Xingcui Zhou et al.
Chemical communications (Cambridge, England), 58(61), 8568-8571 (2022-07-12)
An efficient gold(I)-catalyzed redox cycloisomerization/nucleophilic addition/reduction reaction of o-nitroalkynes with various H-phosphorus oxides is established. Through the intramolecular redox cyclization of o-nitroalkynes and subsequent intermolecular nucleophilic addition/reduction with no external reactant, a variety of arylphosphoryl and alkylphosphoryl indolin-3-ones with high
Yang Yuan et al.
Chemical communications (Cambridge, England), 58(86), 12110-12113 (2022-10-14)
We report here a cooperative Cu/Pd-catalyzed multi-component borocarbonylation of ethylene with aryl iodides. A variety of synthetically useful β-boryl ketones were assembled from the most basic C1 (CO) and C2 (ethylene) building blocks in good yields.
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