Ligand-free Palladium-Catalyzed Carbonylative Suzuki Coupling of Aryl Iodides in Aqueous CH3CN with Sub-stoichiometric Amount of Mo(CO)6 as CO Source
A new method for the synthesis of diaryl and heterodiaryl ketones has been established based on the palladium-catalyzed carbonylative Suzuki coupling approach with sub-stoichiometric Mo(CO)6 as CO source. Using 0.5 mol% of Pd(TFA)2 as catalyst, 0.5 equivalent of Mo(CO)6 as solid carbonyl reagent and 3 equivalent of K3PO4 as base, a wide range of functionalized (hetero)aryl iodides and (hetero)aryl boronic acids could smoothly proceed the carbonylative cross-coupling reaction in aqueous CH3CN at 50 °C, affording the corresponding ketones in good to excellent yields. The newly developed method was easy to operate under mild conditions with high efficiency. (Figure presented.).
Synthesis and structure-activity relationships of benzophenone-bearing diketopiperazine-type anti-microtubule agents
KPU-105 (4), a potent anti-microtubule agent that contains a benzophenone was derived from the diketopiperazine-type vascular disrupting agent (VDA) plinabulin 3, which displays colchicine-like tubulin depolymerization activity. To develop derivatives wit
A phosphine-free carbonylative cross-coupling reaction of aryl iodides with arylboronic acids catalyzed by immobilization of palladium in MCM-41
The phosphine-free heterogeneous carbonylative cross-coupling of aryl iodides with arylboronic acids under an atmospheric pressure of carbon monoxide was achieved in anisole at 80 °C in the presence of a 3-(2-aminoethylamino) propyl-functionalized MCM-41-immobilized palladium(ii) complex [MCM-41-2N-Pd(ii)], yielding a variety of unsymmetrical biaryl ketones in good to high yield. This heterogeneous palladium catalyst exhibited higher activity and selectivity than PdCl2(PPh3)2, can be recovered and recycled by a simple filtration of the reaction solution, and used for at least 10 consecutive trials without any decrease in activity. Our system not only avoids the use of phosphine ligands, but also solves the basic problem of palladium catalyst recovery and reuse.
Carbomylative Suzuki-Miyaura coupling of arylboronic acids with aryl iodides catalyzed by the MCM-41-supported bidentate phosphane palladium(II) complex
The first heterogeneous carbonylative Suzuki-Miyaura cross-coupling reaction of arylboronic acids with aryl iodides under an atmospheric pressure of carbon monoxide has been achieved in anisole at, 80 °C in the presence of a catalytic amount of an MCM-41-supported bidentate phosphane palladium(II) complex (MCM-41-2P-PdII), yielding unsymmetrical biaryl ketones in good-to-high yields. This polymeric palladium catalyst exhibited higher activity and selectivity than fPdCl2(PPh3)2] and can be reused at least 10 times without any decrease in activity. Wiley-VCH Verlag GmbH & Co, KGaA.