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755761

Sigma-Aldrich

Diaqua[1,3-bis(diphenylphosphino)propane]palladium(II) bis(tetrafluoroborate)

95%

Synonym(s):

[Pd(dppp)(H2O)2](BF4)2

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About This Item

Empirical Formula (Hill Notation):
C27H30O2P2Pd · 2BF4
CAS Number:
134668-73-8
Molecular Weight:
728.50
MDL number:
MFCD22417207
UNSPSC Code:
12352300
PubChem Substance ID:
329766139

assay

95%

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

175-200 °C (decomposition)

storage temp.

2-8°C

SMILES string

O.O.[Pd++].F[B-](F)(F)F.F[B-](F)(F)F.C(CP(c1ccccc1)c2ccccc2)CP(c3ccccc3)c4ccccc4

InChI

1S/C27H26P2.2BF4.2H2O.Pd/c1-5-14-24(15-6-1)28(25-16-7-2-8-17-25)22-13-23-29(26-18-9-3-10-19-26)27-20-11-4-12-21-27;2*2-1(3,4)5;;;/h1-12,14-21H,13,22-23H2;;;2*1H2;/q;2*-1;;;+2

InChI key

RJHRHADURPIBJJ-UHFFFAOYSA-N

Application

Versatile Palladium precatalyst for cyclization reactions.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
SHBD1436V
SHBC2300V

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Cationic Palladium Complex-Catalyzed Diastereoselective Tandem Annulation of 2-Iminoarylboronic Acids with Substituted Alkynes: Enantioselective Synthesis of Aminoindene Derivatives by Double Asymmetric Induction
Yu, X.; Lu, X.
Advanced Synthesis & Catalysis, 353, 2805-2813 (2011)
Xufen Yu et al.
Organic letters, 11(19), 4366-4369 (2009-09-02)
Cationic palladium complex [(dppp)Pd(H(2)O)(2)](2+)(BF(4)(-))(2) catalyzed tandem annulation reactions of 2-formylarylboronic acids and allenoates produce the indenol derivatives diastereo- and enantioselectively in a highly efficient way.
Xiuling Han et al.
Organic letters, 12(1), 108-111 (2009-12-09)
High chemoselectivity for the synthesis of two kinds of substituted coumarins controlled by the counteranions of the cationic palladium catalysts is described. The asymmetric version of the reaction for the synthesis of 3-alkylidene dihydrocoumarins is realized with high enantioselectivity.
Xufen Yu et al.
The Journal of organic chemistry, 76(15), 6350-6355 (2011-07-13)
The 1-benzoxepine derivatives were synthesized conveniently by cationic palladium-catalyzed [5 + 2] annulation reaction of 2-acylmethoxyarylboronic acids with allenoates in high yields. This annulation involves the intramolecular nucleophilic addition to ketones without the formation of π-allylpalladium species.
Kun Shen et al.
Organic letters, 14(7), 1756-1759 (2012-03-28)
Cationic Pd(II)-catalyzed enantioselective arylative cyclization of alkyne-tethered enals or enones initiated by carbopalladation of alkynes was developed without the necessity of a redox system.

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