Palladium-Catalyzed Borylation of Phenyl Bromides and Application in One-Pot Suzuki−Miyaura Biphenyl Synthesis

Abstract

The coupling reaction of pinacolborane with various aryl bromides in the presence of a catalytic amount of Pd(OAc)(2) together with DPEphos as ligand and Et(3)N as base provided arylboronates. High yields were obtained in the case of electron-donor substituted aryl bromides. The direct preparation of arylboronates allowed the one-pot, two-step synthesis of unsymmetrical biaryls in high yields. [reaction: see text]

Miyaura Borylations of Aryl Bromides in Water at Room Temperature

“…Spectral data for the following compounds matched previously reported data: 3 , 8 4 , 9 5 , 10 6 , 8 7 , 8 9 , 8 10 , 6 11 , 8 12 , 6 13 , 11 15 , 10 16 , 10 17 . 6 …”

Synthesis of Polycyclic Aromatic Hydrocarbon‐Based Nanovehicles Equipped with Triptycene Wheels

“…[24] Therefore, to isolate the boronic ester, we considered the reaction with bis-pinacolborane in the presence of a palladium catalyst. [25] In all cases, the starting material was recovered in quantitative yield, which again demonstrated the lack of reactivity of this substrate.…”

Preparation of 1,3-dienyl organotrifluoroborates and their Diels–Alder/cross-coupling reactions

“…First a phenyl substituted 2-halodiene (44) was subjected to the cross-coupling reaction with pinacolborane following a protocol similar to the one Colobert and co-workers used in their arylboronates synthesis. 51 Reduced diene (47) was obtained as the major product in this process instead of the expected product (48). In a second attempt to overcome this problem, a diboryl reagent (49) was employed with ligandless palladium catalyst conditions, similar to the approach taken by Zhang and co-workers in their arylboronate synthesis.…”