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

Catalog Number
ACM251567289-1
Product Name
trans-Bromo(N-succinimidyl)bis(triphenylphosphine)palladium(II)
Structure
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CAS
251567-28-9
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Synonyms
251567-28-9;trans-Bromo(N-succinimidyl)bis(triphenylphosphine)palladium(II);[Pd(NCOC2H4CO)(PPh3)2Br];Bromobis(triphenylphosphine)(N-succinimide)palladium(II);SCHEMBL1591406;SC10544;BROMOBIS(PH3P)(N-SUCCINIMIDE)PD(II);trans-Bromo(N-succinimidyl)bis(triphenylphosphine)palladium(II), 97%;
IUPAC Name
bromopalladium(1+);pyrrolidin-1-ide-2,5-dione;triphenylphosphane;
Molecular Weight
808.989g/mol
Molecular Formula
C40H34BrNO2P2Pd;
Canonical SMILES
C1CC(=O)[N-]C1=O.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Br[Pd+];
InChI
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;
Complexity
315
Covalently-Bonded Unit Count
4
Exact Mass
807.028g/mol
H-Bond Acceptor
3
Heavy Atom Count
47
Monoisotopic Mass
807.028g/mol
Rotatable Bond Count
6
Topological Polar Surface Area
35.1A^2
Application
trans-Bromo(N-succinimidyl)bis(triphenylphosphine)palladium(II) serves as an effective catalyst and precatalyst in various Suzuki cross-coupling reactions. Its role is significant in the synthesis of complex organic compounds, such as 6-cyano-2-(3-fluoro-benzyl)-indole-1-carboxylic acid tert-butyl ester, where it facilitates the coupling of 1-boc-6-cyanoindole-2-boronic acid with 3-fluorobenzyl bromide without the need for strong bases or hazardous reagents, thereby reducing protodeboronation. Moreover, it acts as a precatalyst in the Suzuki-Miyaura cross-coupling of alkenyl tosylates and alkenyl MIDA boronates without requiring phosphine ligands. The addition of tricyclohexylphosphine tetrafluoroborate enhances reactivity when working with less activated alkenyl tosylates, making this catalyst versatile and efficient for various synthetic applications.
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