A new route to various substituted fluoren-9-ones has been developed via an efficient Pd-catalyzed carbonylative multiple C–C bond formation. Under a CO atmosphere, using commercially available aryl halides and arylboronic acids as substrates, this three-component reaction proceeded smoothly in moderate to excellent yields with good functional-group compatibility. The mechanistic investigations suggested a sequential process for the reaction that forms o-bromobiaryls in the first stage followed by a cyclocarbonylation reaction. This chemistry has been successfully extended to construct ladder-type oligo-p-phenylene cores.

A mechanistic study on the zinc-promoted coupling between aldehydes and terminal alkynes via nucleophilic addition/Oppenauer oxidation using operando IR, XANES/EXAFS techniques and DFT calculations was demonstrated. It was determined that a bimetallic zinc complex was the active species.

Using 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) as the oxidant, we communicate an efficient oxidative C-N coupling of benzylic C-H bonds with amides to afford a series of amination products in good yields. A wide range of functional groups as well as various sulfonamides and carboxamides are well tolerated. Moreover, this reaction involves both the challenging C-H functionalization and C-N bond formation.

A facile base-promoted sulfur-centered radical generation mode and a single-step protocol for the synthesis of thiophene derivatives using 1,3-diynes via the interaction between elemental sulfur and NaOtBu has been reported. EPR experiments revealed that the trisulfur radical anion acts as a key intermediate of this process. A plausible mechanism has been proposed.

Thiophene, as one of the most common structural units in functional organic materials, was efficiently installed into π-conjugated systems via a simple, ligand-free Suzuki coupling. The reaction proceeded with high efficiency and good functional-group compatibility while requiring 0.02 mol% of palladium catalyst.

A mechanistic study on the zinc-promoted coupling between aldehydes and terminal alkynes via nucleophilic addition/Oppenauer oxidation using operando IR, XANES/EXAFS techniques and DFT calculations was demonstrated. It was determined that a bimetallic zinc complex was the active species.