CAS 185812-86-6 Bis (tri-t-butylphosphine) palladium bromide (I), dimer

Synonyms

MFCD04114019; 185812-86-6; CTK8C5468; palladium(I) tri-tertbutylphosphine bromide; PUBCHEM_71317307; Palladium(I) tri-tert-butylphosphine bromide;

IUPAC Name

palladium;tritert-butylphosphane;bromide;

Molecular Weight

388.646g/mol

Molecular Formula

C12H27BrPPd-;

Canonical SMILES

CC(C)(C)P(C(C)(C)C)C(C)(C)C.[Br-].[Pd];

InChI

InChI=1S/C12H27P.BrH.Pd/c1-10(2,3)13(11(4,5)6)12(7,8)9;;/h1-9H3;1H;/p-1;

InChI Key

WIADNXKBAGKNOT-UHFFFAOYSA-M;

Complexity

128

Covalently-Bonded Unit Count

Exact Mass

387.007g/mol

Formal Charge

-1

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

387.007g/mol

Rotatable Bond Count

Topological Polar Surface Area

0A^2

Application

Bis(tri-t-butylphosphine)palladium bromide (I), dimer, serves as an effective catalyst in facilitating a variety of coupling reactions. It is particularly useful for activating aryl chlorides and sterically hindered or electron-rich aryl and vinyl bromides and iodides, and is especially efficacious in challenging amination processes. This compound plays a crucial role in Suzuki coupling, Negishi coupling, and Buchwald-Hartwig aminations. It is adept at catalyzing the formation of C-C, C-N, and C-S bonds, and is essential for gamma-arylation of alpha, beta-unsaturated esters as well as diastereoselective arylation of 4-substituted cyclohexyl esters. Additionally, it supports aromatic halide substitution reactions and is instrumental in achieving rapid room temperature alkylation of unactivated hindered aryl bromides with arylboronic acids. Its applications extend to aryl bromide-silyl ketene acetal coupling, intermolecular α-arylation of zinc amide enolates, α-vinylation of carbonyl compounds, and thiol coupling of heteroaromatic aryl bromides.

February 4, 2025

Exceptional Catalyst for Challenging Reactions

We've been leveraging Bis(tri-t-butylphosphine) palladium bromide (I), dimer from Alfa Chemistry in our research. Exceptional for aryl bromide activation and complex couplings. Perfect for room-temperature alkylations and Buchwald-Hartwig aminations!