Phosphine-free palladium-catalyzed cross-coupling of tris(1-naphthyl)borane with aryl halides and iodonium salts

Palladium-Catalyzed Cross-CouplingReaction of Potassium Diaryldifluoroborates with Aryl Halides

“…1 Aryl-aryl bond formation has become a most important tool of organic synthesis because these bonds are found in natural products as well as in numerous biologically active parts of pharmaceuticals and agrochemicals. [3][4][5] Among these organoboron compounds, triarylboranes 6 and tetrarylborates 7 were demonstrated as the multiple aryl transfer reagents from boron in crosscoupling reaction. [3][4][5] Among these organoboron compounds, triarylboranes 6 and tetrarylborates 7 were demonstrated as the multiple aryl transfer reagents from boron in crosscoupling reaction.…”

Aryl Diazonium versus Iodonium Salts: Preparation, Applications and Mechanisms for the Suzuki–Miyaura Cross‐Coupling Reaction

“…Based on the interesting results of Kang and co‐workers with sterically‐hindered boronic derivatives, Bumagin and Tsarev synthesized 1‐arylnaphthalenes, starting from tris(1‐naphthyl)borane and symmetrical diaryliodonium salts, with PdCl 2 as catalyst (1 mol%) 66. Under ligand‐free and basic aqueous conditions at 70 °C, and using a borane:iodinane ratio of 2:3, all naphthyl groups of the borane and both aryl groups of the iodonium salt could be coupled in high yields (Scheme ).…”

“… Cross‐coupling of the diphenyl tetrafluroborate iodonium salt with the tris(1‐naphthyl)borane by Bumagin et al 66…”

Alcoholic solvent‐assisted ligand‐free room temperature Suzuki–Miyauracross‐coupling reaction

“…Phosphine‐free ('ligandless') palladium catalysis was suggested for the first time by Bumagin et al . in the early 1980s for Stille cross‐coupling reactions and later for Suzuki reactions in water and aqueous media . Consequently, various ligand‐free conditions have been applied in palladium‐catalysed Suzuki–Miyaura reactions which unlock new opportunities in catalysis for this vital reaction …”