Palladium-Catalyzed Synthesis of Dibenzofuran Derivatives

The dibenzofuran scaffold, characterised by two benzene rings fused to a central furan, is a privileged motif in organic materials, pharmaceuticals and agrochemicals. Palladium catalysis has emerged as a versatile platform for constructing this heterocycle with high efficiency and broad functional‐group tolerance. Key strategies centre on cross-coupling and intramolecular C–O bond formation: for example, Suzuki–Miyaura reactions between 2-halophenols (or their masked equivalents) and aryl boronic acids followed by oxidative cyclisation, or Negishi couplings of aryl zincates derived from directed ortho-lithiation precursors. Advances in C–H activation have further streamlined access to highly substituted frameworks via direct oxidative annulation of phenolic substrates under mild, aerobic conditions. Cascade and one-pot sequences integrating multiple palladium-catalysed steps accelerate library synthesis and enable late-stage diversification of core and peripheral substituents. Collectively, these methodologies afford modular routes to dibenzofurans bearing halogen, alkyl, alkoxy and heteroaryl groups, underpinning applications in organic electronics, natural-product synthesis and bioactive lead generation.

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Palladium-Catalyzed Synthesis of Dibenzofuran Derivatives publication trend

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Technical terms

Suzuki–Miyaura coupling: Palladium-catalysed cross-coupling between organoboron reagents and aryl (or vinyl) halides to form C–C bonds.

Negishi coupling: Palladium-catalysed reaction of organozinc reagents with aryl or vinyl halides to form C–C bonds under mild conditions.

Directed ortho-lithiation: Lithiation at the ortho position of an aromatic substrate guided by a directing group, enabling subsequent metalation or coupling.

Intramolecular nucleophilic aromatic substitution (SNAr): Intramolecular displacement of a leaving group on an aromatic ring by an adjacent nucleophile, forming a new ring.

C–H activation: Palladium-catalysed cleavage of a C–H bond and coupling with a partner (e.g. C–O or C–C bond formation) to build complex frameworks directly from C–H precursors.

References

1. Synthesis of Benzofuropyridines and Dibenzofurans by a Metalation/Negishi Cross-Coupling/SNAr Reaction Sequence. The Journal of Organic Chemistry (2022).