Dialkylbiaryl phosphines are a valuable class of ligand for Pd-catalyzed amination reactions and have been applied in a range of contexts. This perspective attempts to aid the reader in the selection of the best choice of reaction conditions and ligand of this class for the most commonly encountered and practically important substrate combinations.

Dialkylbiaryl phosphines in Pd-catalyzed amination: a user's guide

Pd-Catalysed Suzuki–Miyaura cross-coupling of aryl chlorides at low catalyst loadings in water for the synthesis of industrially important fungicides

Efficient and Practical Synthesis of 3′,4′,5′-Trifluoro-[1,1′-biphenyl]-2-amine: A Key Intermediate of Fluxapyroxad

A new ligand is designed and synthesized in two steps starting from α-formyl 3-pyrrolyl BODIPY. In the first step, the α-formyl 3-pyrrolyl BODIPY was condensed with 1,2-diaminobenzene in toluene at reflux and afforded α-benzimidazole 3-pyrrolyl BODIPY in 16% yield. In the second step, α-benzimidazole 3-pyrrolyl BODIPY was decomplexed upon being treated with Lewis acid AlCl3 and afforded the desired ligand α-benzimidazole 9-pyrrolyl dipyrromethene. However, the ligand was not very stable and reacted further with PdCl2 in CH3CN for 1 h at reflux followed by recrystallization and afforded a novel bis-palladium complex of α-benzimidazole 9-pyrrolyl dipyrromethene in 36% yield. The bis-palladium complex was characterized and studied by high-resolution mass spectrometry, one- and two-dimensional nuclear magnetic resonance, X-ray crystallography, absorption, and density functional theory/time-dependent DFT (DFT/TD-DFT) studies. The X-ray structure revealed that two ligands and two Pd(II) ions were involved in forming a unique complex in which each Pd(II) ion was coordinated to three pyrrole N atoms of the first ligand and the benzimidazole N atom of the second ligand in a distorted square planar geometry. The absorption spectrum of the bis-palladium complex shows ill-defined, broad, and less intense bands in the region of 345-425 nm along with split bands in the higher-wavelength region of 600-630 nm. The bis-palladium complex was nonfluorescent, and the results of DFT/TD-DFT studies were in agreement with the experimental observations. The preliminary studies indicated that the bis-palladium complex can act as an efficient catalyst for coupling different aryl bromides with phenylboronic acid.

Bis-Palladium Complex of α-Benzimidazole 9-Pyrrolyl Dipyrromethene: Synthesis, Structure, and Spectral and Catalytic Properties.

In the absence of ligand, Cs2CO3-promoted cross-coupling reaction of arenes with cyano-/nitro-substituted aryl halides in DMSO affording biaryls is reported. The cyano/nitro group in biaryls is useful and convenient for further transformation. The formation of dibenzofurans resulting from the reactions between arenes and 1-bromo-2-iodobenzene is also reported. On the basis of control experiments and theoretical studies, a radical mechanism is proposed for the formation of biaryls.

Biaryl Formation via Base-Promoted Direct Coupling Reactions of Arenes with Aryl Halides.

An easily available Pd(OAc)2/(2-(anthracen-9-yl)-1H-inden-3-yl) dicyclohexylphosphine/toluene/iPrOH/water catalytic system was developed, which shows high catalytic activity in the Suzuki–Miyaura cross-coupling reactions of a diverse array of aryl and heteroaryl chlorides with Pd loadings down to 0.01 mol%.

An active catalytic system for Suzuki–Miyaura cross-coupling reactions using low levels of palladium loading

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An active catalytic system for Suzuki–Miyaura cross-coupling reactions using low levels of palladium loading