title: Oxygenative and Dehydrogenative [3 + 3] Benzannulation Reactions of α,β-Unsaturated Aldehydes and γ-Phosphonyl Crotonates Mediated by Air: Regioselective Synthesis of 4-Hydroxybiaryl-2-carboxylates.
abstract: 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.
authors: Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology , Hyderabad 500 007, India.
authors: Prabhakar Ramchandra
authors: PR
authors: Joshi
authors: Centre for X-ray Crystallography, CSIR-Indian Institute of Chemical Technology , Hyderabad 500 007, India.
authors: Jagadeesh Babu
authors: JB
authors: Nanubolu
authors: Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology , Hyderabad 500 007, India.
authors: Rajeev S
authors: RS
authors: Menon
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003437:Crotonates / Q000737:chemistry*; D015394:Molecular Structure; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D002264:Carboxylic Acids; D003437:Crotonates; D010636:Phenols