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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Regio-reversed alkenyl-arylation of ynamides via 1,3-olefin shift
Saumya Verma1, Manoj Sethi1, Akhila K Sahoo1
1School of Chemistry, University of Hyderabad 500046 India akhilchemistry12@gmail.com akssc@uohyd.ac.in.
None:
A cationic Pd-catalysed multicomponent reaction enables the regio-reversed alkenyl-arylation of ynamides through a migratory difunctionalization strategy. A stereoselective 1,3-olefin shift of a keteniminium-alkenyl-Pd intermediate governs the carbopalladation pathway, generating a vinylic Pd species that subsequently couples with aryl boronates. This protocol offers streamlined access to highly substituted branched dienes, trienes, and divinyl ethylene (DVE) derivatives with excellent regio- and stereocontrol. The broad substrate scope, scalability, and mechanistic insights highlight the synthetic potential of this transformation. Additionally, the photophysical properties of these conjugated systems were examined, underscoring their potential as functional materials for optoelectronic applications.
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