Ceric ammonium nitrate (CAN)-promoted oxidative -cyclization of unactivated biaryl ynones with -centered radicals (SCN/SCF) to access spiro[5,5]trienones has been established. This approach displayed excellent regioselectivity towards spirocyclization and tolerated a variety of functional groups. Dearomatization of hitherto unknown aryl/heteroaryl groups is also disclosed. DMSO is employed as a low-toxicity, inexpensive solvent as well as a source of oxygen.

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http://dx.doi.org/10.1039/d3ob00974bDOI Listing

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