Regioselective synthesis of substituted arenes via aerobic oxidative [3 + 3] benzannulation reactions of α,β-unsaturated aldehydes and ketones.
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.
†Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500 007, India.
Prabhakar Ramchandra
PR
Joshi
†Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500 007, India.
Sridhar
S
Undeela
†Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500 007, India.
Doni Dhanoj
DD
Reddy
‡Centre for Nuclear Magnetic Resonance, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500 007, India.
Kiran Kumar
KK
Singarapu
†Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500 007, India.
Rajeev S
RS
Menon