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Gold‐Catalyzed Arylative Cope Rearrangement

Bidisha Paroi, Chayanika Pegu, Manoj V. Mane, Manoj V. Mane, Nitin T. Patil

2024Angewandte Chemie International Edition20 citationsDOI

Abstract

Abstract Cope rearrangements have garnered significant attention owing to their ability to undergo structural reorganization in stereoselective manner. While substantial advances have been achieved over decades, these rearrangements remained applicable exclusively to parent 1,5‐hexadienes. Herein, we disclose the gold‐catalyzed arylative Cope rearrangement of 1,6‐heptadienes via a cyclization‐induced [3,3]‐rearrangement employing ligand‐enabled gold redox catalysis. Detailed mechanistic investigations including several control experiments, cross‐over experiment, HRMS analysis, 31 P NMR and DFT studies have been performed to underpin the mechanism.

Topics & Concepts

CatalysisChemistryCombinatorial chemistryOrganic chemistryCatalytic Alkyne Reactions
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