Dedicated to Prof. Viktor V. Zhdankin for his outstanding contribution to Hypervalent Iodine Chemistry. Copper(I)-catalyzed N-arylation (both N 1-and N 3-) of hydantoins with diaryliodonium salts as aryl partners at room temperature is reported. The transformation allows diverse scopes on both hydantoins and diaryliodonium salts delivering functionalized N 3-arylated products under mild reaction conditions. The presence of hydrogens at C 5-and N 1-position of the hydantoin does not lead to other side products. Chiral hydantoins can also be synthesized via this methodology. Sterically complicated ortho-substituted diaryliodonium salts are tolerated and delivered challenging ortho-arylated products. In addition, this strategy can also be effectively extended to N 1-arylation of hydantoins.
The pyrrole and indole derivatives are functionalized via a green initiative with dimethylmalonate derived phenyl iodonium ylide 4a in presence of blue LED via C-H functionalization of the respective heterocycles...
An efficient copper-catalyzed solvent-free multicomponent reaction for pyridine derivatives, iodonium ylides, and 1,4-quinones is developed via a room-temperature ball milling technique. The reported protocol provides a sustainable synthesis of isoindolo[2,1-a]pyridine/isoquinoline class of molecules in good to excellent yield in a mixer mill (RETSCH MM400) engaging the commercially available copper acetate (Cu(OAc) 2 ) as a catalyst without the use of organic solvents. It tolerates a myriad of electron-rich and electron-deficient functionalities on the pyridine moiety. The scalability of the protocol was illustrated by successfully performing the reaction in the gram scale. The photoluminescence and related cellular study revealed that these can be used as a fluorescent chromophore-based cellular probe. A clean reaction profile and a facile experimental setup that is devoid of anhydrous reaction conditions and toxic organic solvents have established the advantages of this strategy over the reported process.
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