ABSTRACT
A photocatalytic decarboxylative aminoalkylation of 4-cyanopyridines with N-arylglycines is achieved, providing 4-(aminomethyl)pyridine derivatives in moderate to good yields. This organic photocatalytic reaction undergoes a radical-radical cross-coupling process under redox-neutral conditions, featuring simple operation, readily available N-arylglycines and a broad substrate scope. Mechanistic investigations indicated that a proton-coupled electron-transfer process was involved to enable the single electron transfer between the reduced photocatalyst and 4-cyanopyridine in the presence of N-arylglycines.
ABSTRACT
A photocatalytic trifluoromethylation/cyclization reaction of N-allyl and N-homoallyl aldehyde hydrazones with trifluoromethyl thianthrenium triflate was developed for the synthesis of trifluoromethylated dihydropyrazoles and tetrahydropyridazines. Besides, PhI(O2CCHF2)2 was employed to realize the construction of difluoromethylated dihydropyrazoles and tetrahydropyridazines. These protocols exhibit a broad substrate scope and good functional group tolerance.
ABSTRACT
A photocatalytic radical carbophosphorylation/cyclization of N-homoallyl aldehyde hydrazones with phosphine oxides was developed under metal-free conditions, achieving phosphorylated tetrahydropyridazines in yields up to 95%. Phosphorylated dihydropyrazoles were also constructed, by reacting N-allyl aldehyde hydrazones with phosphine oxides under the same conditions.
ABSTRACT
A new kind of building unit, 3-(2-isocyanophenyl)quinazolin-4(3H)-ones, was designed and synthesized for the construction of novel quinoxalino[2,1-b]quinazolinones. The radical cyclization of 3-(2-isocyanophenyl)quinazolin-4(3H)-ones with ethers afforded ether-substituted tetracyclic quinoxalino[2,1-b]quinazolinones under photocatalytic and metal-free conditions. In the process, the isocyano accepts a carbon radical to give an imidoyl radical, which adds to the electron-deficient CîN bond in quinazolin-4(3H)-one.