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trans-Bromo(N-succinimidyl)bis(triphenylphosphine)palladium(II)

Name: <I>trans</I>-Bromo(<I>N</I>-succinimidyl)bis(triphenylphosphine)palladium(II)
Brand: ALDRICH

97%

Synonym(s):

Bromobis(triphenylphosphine)(N-succinimide)palladium(II), [Pd(NCOC₂H₄CO)(PPh₃)₂Br]

About This Item

Empirical Formula (Hill Notation):

C₄₀H₃₄BrNO₂P₂Pd

CAS Number:

251567-28-9

Molecular Weight:

808.98

NACRES:

NA.22

PubChem Substance ID:

24883292

UNSPSC Code:

12352300

MDL number:

MFCD06411335

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Properties

assay

97%

form

solid

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

223-228 °C (dec.) (lit.)

SMILES string

Br[Pd]N1C(=O)CCC1=O.c2ccc(cc2)P(c3ccccc3)c4ccccc4.c5ccc(cc5)P(c6ccccc6)c7ccccc7

InChI

1S/2C18H15P.C4H5NO2.BrH.Pd/c2*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;6-3-1-2-4(7)5-3;;/h2*1-15H;1-2H2,(H,5,6,7);1H;/q;;;;+2/p-2

InChI key

KYQYWUJRFOCJEW-UHFFFAOYSA-L

Description

Application

Catalyst for C-C bond formation, e.g. Stille coupling reaction and Suzuki coupling.

trans-Bromo(N-succinimidyl)bis(triphenylphosphine)palladium(II) may be used in the following processes:

As a catalyst for the preparation of 6-cyano-2-(3-fluoro-benzyl)-indole-1-carboxylic acid tert-butyl ester via Suzuki cross-coupling reaction between 1-boc-6-cyanoindole-2-boronic acid and 3-fluorobenzyl bromide. This method does not involve the use of strong bases or toxic reagents and also the use of this catalyst minimizes protodeboronation.
As a precatalyst for the Suzuki-Miyaura cross-coupling reaction between alkenyl tosylates and alkenyl MIDA boronates in the absence of phosphine ligands. For less activated alkenyl tosylate, the addition of tricyclohexylphosphine tetrafluoroborate improves the reactivity.

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Suzuki-Miyaura cross-coupling of alkenyl tosylates with alkenyl MIDA boronates.

Luthy M and Taylor RJK.

Tetrahedron Letters, 53(27), 3444-3447 (2012)

Palladium-catalyzed benzylation of N-Boc indole boronic acids.

Kearney AM, et al.

Tetrahedron Letters, 51(17), 2281-2283 (2010)

Simple palladium(II) precatalyst for Suzuki-Miyaura couplings: efficient reactions of benzylic, aryl, heteroaryl, and vinyl coupling partners.

Michael J Burns et al.

Organic letters, 9(26), 5397-5400 (2007-12-01)

trans-PdBr(N-Succ)(PPh3)2 (1) is a universally effective precatalyst for Suzuki-Miyaura cross-couplings of benzylic halides with aryl- or heteroarylboronic acids. Substituted aryl halides and halogenated cyclic enones can be cross-coupled with aryl- or vinylboronic acids in excellent yields. Catalyst recycling is also

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