Facile conversion of α,β-unsaturated aldehydes and ketones into highly substituted arenes via a base-mediated, completely regioselective, air-oxidative [3 + 3] benzannulation reaction with readily available 4-sulfonylcrotonates or 1,3-bisphenylsulfonylpropene is reported. The reaction can also be carried out as a one-pot, three-component operation using 4-bromocrotonates, aryl sulfinates, and cinnamaldehyde. This open-flask, metal-free reaction does not require anhydrous solvents, proceeds under mild conditions, and uses atmospheric oxygen as the oxidant to afford high yields of the 3-(arylsulfonyl)benzoic acid esters.
Regioselective synthesis of 4-hydroxybiphenyl-2-carboxylates via the base-mediated oxygenative [3 + 3] benzannulation reaction of α,β-unsaturated aldehydes and γ-phosphonyl crotonates is reported. A hydroxyl group is installed in the final product on the originally phosphorus-bound carbon via a novel oxygenative and dehydrogenative transformation. The reaction proceeds rapidly in an open flask, uses atmospheric oxygen as an oxidant, and affords good yields of substituted biaryl phenols.
Regioselective synthesis of 3‐arylsulfonyl benzophenone derivatives via base mediated, aerial‐oxidative [3+3] benzannulation of α,β‐unsaturated aldehydes and 4‐sulfonyl butenones is reported. A variety of readily available acyclic building blocks are transformed into substituted biaryl ketones in this benzannulation reaction. The reaction proceeds under mild conditions in an open flask and uses atmospheric oxygen as oxidant to afford good yields of the products. Analogous benzannulation reactions of chalcone afforded highly substituted m‐terphenyl‐benzophenone derivatives.
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