Oxidative C−C/P−H cross-coupling is achieved via Pd-catalyzed decarbonylative cross-coupling of aroylhydrazides with P(O)H compounds. The unique cooperative reaction system, especially the Brønsted acid and bidentate phosphine ligand, allows the selective activation of the inert C−C bond and the suppression of the undesired oxidation and coordination of >P(O)−H compounds, leading to a general oxidative synthesis of aryl phosphorus compounds from easily available substrates.

For the first time, the selective oxidative transformation of 2-naphthols with terminal alkynes is disclosed, which enables the straightforward synthesis of 2-arylnaphtho[2,1-b]furans in satisfactory yields under metal-free conditions. Mechanistic study suggests that the reaction proceeds via free-radical-mediated sp(2)-C-H bond activation, C-C coupling, and C-O cyclization.

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The scalable reaction is successfully performed starting from functionalized 2‐naphthols and aryl alkynes, but fails using 1‐naphthol, phenol or biphenol and alkyl substituted or internal alkynes.