Palladium-catalyzed carbonylative synthesis and theoretical study of elongated tubular cavitands

27 Years of Catalytic Carbonylative Coupling Reactions in Hungary (1994–2021)

“…Moreover, carbonylative syntheses applied on a cavitand skeletons were not mentioned in the literature at all, with the exception of the works of our research group. In the recent ten years, our research group had developed several palladium-and copper-catalyzed reactions on a cavitand sceleton [86][87][88][89], including palladium-catalyzed aminocarbonylation [90][91][92][93].…”

“…The c14 deepend cavitand bearing also four iodoaryl groups on the upper rim is even larger than c1 cavitand. Despite the molar mass of c14 is above 2000 g/mol hence both solubility and steric problems could have been expected during the reaction, c14 was also suitable as substrate for aminocarbonylation [93] and successful reactions were performed with five different amines (Figure 20) at atmospheric and high pressure (90 bar) also. In agreement with the previous results, the high carbon monoxide pressure was favorable for the formation of the ketocarboxamide products, while at atmospheric pressure the carboxamide products were formed in larger amounts.…”

Synthesis of Novel Cavitand Host Molecules via Palladium-Catalyzed Aryloxy- and Azidocarbonylation

“…In the last decade, our research group had developed and described several palladium- and copper-catalyzed homogeneous catalytic processes on a cavitand scaffold, including the palladium-catalyzed aminocarbonylation [ 13 ], copper-catalyzed azide-alkyne cycloaddition (CuAAC) [ 14 , 15 ] and Sonogashira or Suzuki-Miyaura coupling [ 16 ]. It has been proven that homogeneous catalytic processes can be easily adopted for cavitands, and similar results can be expected in terms of both reactivity and selectivity as in the case of small molecules.…”

“…Primary carboxamides as stable final products were obtained using this protocol. Continuing our investigations on the synthesis of functionalized cavitands [ 13 , 15 , 16 , 35 ], with the aim of their application in host-guest chemistry, homogeneous catalytic reactions were applied for the introduction of novel functionalities. The synthetic strategy of these supramolecular entities is based on the combination of high-yielding conventional procedures and highly selective homogeneous catalytic reactions.…”