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What is di-chlorobis[(1,2,3-)-1-phenyl-2-propenyl]dipalladium(ii)?

Feb 12，2020

Di-chlorobis[(1,2,3-)-1-phenyl-2-propenyl]dipalladium(ii) is an important organic regant for the use of transition-metal-mediated organic syntheses. Di-chlorobis[(1,2,3-)-1-phenyl-2-propenyl]dipalladium(ii) can be used as a catalyst for the ammonia cross-coupling reactions to synthesize arylamines and conversion of aryl triflates to fluorides.
 
In addition, di-chlorobis[(1,2,3-)-1-phenyl-2-propenyl]dipalladium(ii) is an important organic intermediate to synthesize (π-Allyl)Pd complexes containing N-heterocyclic carbene and pseudohalogen ligands. In transition-metal-mediated organic syntheses, Pd-catalyzed C–C cross-coupling reactions are widely utilized. In particular, palladium compounds containing labile ligands such as C,N-donor ligands have emerged as efficient precatalysts for Suzuki–Miyaura cross-coupling reactions. Furthermore, to enhance catalytic efficiency in the catalytic reactions, several studies on cyclopalladated compounds containing N-heterocyclic carbenes (NHCs), one of the many sterically and/or electronically beneficial ligands, were used. Pseudohalogen ligands are known to be better leaving groups than halogen ligands in catalytic reactions. Their catalytic activity was dependent on the supporting ligand, a tertiary phosphane or an NHC ligand. For example, compounds with an NHC ligand showed higher catalytic activity for aryl chlorides than those with a combinationof C,N-donor and tertiary phosphane ligands [1].
 
In using [{Pd (cinnamyl)Cl}2]/Mor-DalPhos precatalyst mixtures, electron-rich, electron-poor, and heterocyclic products of ammonia monoarylation were prepared (50–110OC) in high isolated yields. Mor-DalPhos has also been found to be useful in facilitating the Pd-catalyzed monoarylation of hydrazine, acetone, and other carbonyl compounds in chemoselective and aqueous BHA chemistry, as well as in the Au-catalyzed hydroamination of internal alkynes with dialkylamines. Whereas the room-temperature BHA of aryl chlorides with ammonia was not successful when using [{Pd (cinnamyl)Cl}2]/Mor-DalPhos precatalyst mixtures, unprecedented room-temperature transformations of a small number of aryl chlorides were achieved with good monoarylation selectivity by use of the chlorobenzene oxidative addition product [(k2-P,N-Mor-Dal-Phos)Pd(Ph)Cl] as a precatalyst. It is possible to overcome the limitations of other catalysts which include substrate-scope challenges with respect to the monoarylation of electronically deactivated and sterically unhindered aryl chloride substrates, the frequent requirement of relatively high reaction temperatures.[2]

References

1.Kim HK et al. (π-Allyl)Pd Complexes Containing N-Heterocyclic Carbene and Pseudohalogen Ligands – Synthesis, Reactivity toward Organic Isothiocyanates and Isocyanides, and Their Catalytic Activity in Suzuki–Miyaura Cross-Couplings[J]. Eur. J. Inorg. Chem. 2013, 4958–4969
2. Alsabeh PG et al. An Examination of the Palladium/Mor-DalPhos Catalyst System in the Context of Selective Ammonia Monoarylation at Room Temperature[J]. Chem. Eur. J. 2013, 19, 2131 – 2141.
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