CAN‐Supported Chemoselective Oxidative Conversion of α‐Aroylketene‐(S, S)‐acetals to Aryl Carboxylic Acids. Issue 7 (6th March 2017)

• Record Type: Journal Article
• Authors: Babu, Seenivasagaperumal Sriram; Shanmugam, Sivakumar
• Is Part Of: ChemistrySelect. Volume 2:Issue 7(2017)
• Page Start: 2330
• Page End: 2334
• Publication Date: 2017-03-06
• Subjects: α-C-H bond cleavage -- Ceric ammonium nitrate -- Chemoselectivity -- Internal nitrate ligand -- Ketene-(S, S)-acetal; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201700107
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Chemoselective oxidative conversion of α ‐aroylketene‐(S, S)‐acetals to aryl carboxylic acids in the presence of Ceric ammonium nitrate (CAN) has been achieved under mild reaction condition. The internal nitrate ligand present in CAN acted as an oxidant and favored selective conversion of α ‐aroylketene‐(S, S)‐acetals to aryl acid. α ‐Hydrogen is necessary to initiate radical by Ce(IV) via α ‐C‐H bond cleavage. The current synthetic strategy is compatible for various aromatic groups under mild conditions. The method is appropriate for electron rich as well as deficient α, β ‐unsaturated system. Abstract : Chemoselective oxidative conversion of α ‐aroylketene‐(S, S)‐acetals to aryl carboxylic acids in the presence of CAN under mild reaction condition. The internal nitrate ligand present in CAN acted as an oxidant and favored selective conversion of α ‐aroylketene‐(S, S)‐acetals. α ‐Hydrogen is necessary to initiate radical by Ce(IV) via α ‐C‐H bond cleavage. The method is appropriate for electron rich as well as deficient α, β ‐unsaturated system.