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Updated: Sep 15, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Deconstructive [4 + 3] Annulation of Isatin-Derived α-Keto Amides with CF3-Allyl-Pd Species
Chiliveru Priyanka1,2, Rami Sateesh1,2, Chavakula Nagababu1,2
1Fluoro-Agro Chemicals Division, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India.
Abstract:
The catalytic one-pot cascade reaction is a powerful strategy for constructing complex molecules with high regioselectivity. Herein, we present a cascade allylative double intramolecular cyclization (ADIC) for synthesizing benzopyrroloazepines via a deconstructive [4 + 3] annulation of isatin-derived α-keto amides with CF3-allyl-Pd species. This transformation efficiently integrates isatin ring opening, Tsuji-Trost allylation, and double intramolecular cyclizations involving three C-F bond disconnections. The π-CF3-allyl-Pd complexes act as a three-carbon source, while strategic CF3 substitution plays a crucial role in achieving exclusive regioselectivity.
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