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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
From 1,2-Diborylalkenes to Functionalized Indenols: Tandem Suzuki Coupling-Intramolecular Cyclization
Malavath Sravani1,2, Kummari Kunta Harshitha1, Jayaram Vankudoth1
1Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad500 007, India.
Abstract:
A concise and efficient domino strategy for the synthesis of symmetrically 2,3-disubstituted indenols has been developed via palladium-catalyzed Suzuki coupling of readily accessible 1,2-diborylalkenes with substituted 2-bromoaryl carbonyl compounds. The reaction proceeds efficiently, with palladium playing a dual role by mediating C-C bond formation and promoting subsequent intramolecular cyclization through nucleophilic addition of the boronic ester to the carbonyl. Furthermore, a Lewis acid-promoted regioselective approach to 2-substituted indenols and methoxyindenes from terminal 1,2-diborylalkenes via Suzuki-Miyaura coupling is disclosed under mild conditions.
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