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Merck
CN

643742

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

97%

Synonym(s):

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

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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

Key Documents

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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

SMILES string

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

InChI key

KYQYWUJRFOCJEW-UHFFFAOYSA-L

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.)

Application

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

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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Certificates of Analysis (COA)

Lot/Batch Number
SHBF4964V
SHBF0172V
SHBB9952V
59496EK
92096TJ

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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)
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
Palladium-catalyzed benzylation of N-Boc indole boronic acids.
Kearney AM, et al.
Tetrahedron Letters, 51(17), 2281-2283 (2010)

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