Photoinduced Three-Component Difluoroamidosulfonylation/Bicyclization: A Route to Dihydrobenzofuran Derivatives.

A visible-light-induced photocatalyst-free three-component radical cascade bicyclization has been achieved to obtain diverse difluoroamidosulfonylated dihydrobenzofurans in moderate to good yields. This protocol avoids potential toxicity and the tedious removal procedure for photocatalysts and also features mild reaction conditions and a good functional group tolerance. Moreover, mechanistic investigations reveal the formation of a charge-transfer complex and the involvement of an intramolecular 1,5-hydrogen atom transfer process in this transformation.

Direct synthesis of indazole derivatives via Rh(III)-catalyzed C-H activation of phthalazinones and allenes.

A novel Rh(III)-catalyzed annulation of phthalazinones or pyridazinones with various allenes was developed, leading to the formation of indazole derivatives bearing a quaternary carbon in moderate to good yields. The targeted products were synthesized via sequential C-H activation and olefin insertion, followed by ß-hydride elimination and intramolecular cyclization. The synthetic protocol proceeded efficiently with broad functional group tolerance, high atom efficiency and high Z-selectivity. The practicability of this method was proved by synthetic transformation.

Copper-Catalyzed Phosphorylation of 2,3-Allenoic Acids and Phosphine Oxide: Access to Phosphorylated Butenolides.

We investigated a novel Cu-catalyzed annulation of 2,3-allenoic acids with diphenylphosphine oxide, leading to the formation of 4-phosphate butenolides in up to 88% yield. The formation of the C-P bond provides new avenues for the functionalization of different furan-2(5H)-ones, with favorable features such as suitable functional group tolerance and mild synthesis conditions.

Palladium-Catalyzed [2 + 2 + 1] Annulation of Alkyne-Tethered Aryl Iodides with Diaziridinone: Synthesis of 3,4-Fused Tricyclic Indoles.

A novel palladium-catalyzed [2 + 2 + 1] annulation of alkyne-tethered aryl iodides with diaziridinone was developed, leading to the formation of 3,4-fused tricyclic indoles. From a mechanistic standpoint, the formation of fused tricyclic indole scaffolds involved C,C-palladacycles, which were synthesized through the intramolecular reaction of aryl halides and alkynes. The cascade reaction described herein could be carried out with a broad range of substrates and provided various 3,4-fused tricyclic indoles with yields up to 98%.

Rh(iii)-catalyzed, hydrazine-directed C-H functionalization with 1-alkynylcyclobutanols: a new strategy for 1H-indazoles.

Rh(iii)-catalyzed coupling of phenylhydrazines with 1-alkynylcyclobutanols was realized through a hydrazine-directed C-H functionalization pathway. This [4+1] annulation, based on the cleavage of a Csp-Csp triple bond in alkynylcyclobutanol, provides a new pathway to prepare diverse 1H-indazoles under mild reaction conditions.