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Palladium‐Catalyzed Domino Synthesis of 2,3‐Difunctionalized Indoles via Migratory Insertion of Isocyanides in Batch and Continuous Flow
Author(s) -
Chen Su,
Oliva Monica,
Van Meervelt Luc,
Van der Eycken Erik V.,
Sharma Upendra K.
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100339
Subject(s) - chemistry , palladium , isocyanide , oxindole , migratory insertion , domino , aryl , combinatorial chemistry , cascade reaction , nucleophile , indole test , triple bond , quaternary carbon , catalysis , stereochemistry , organic chemistry , alkyl , double bond , enantioselective synthesis
We report, herein, a palladium‐catalyzed cascade comprising carbopalladation, migratory insertion of isocyanide and triple bond activation followed by a nucleophilic attack (OR − ) to construct difunctionalized acyl indoles. The process involves multiple bond formations via key palladium‐chemistry steps, to construct these bis‐heterocycles containing two privileged scaffolds (indole and oxindole) in a single operational step, along with attempts to generate enantioselectivity at a quaternary carbon center. The methodology also demonstrates a continuous‐flow process to synthesize aryl isocyanides within minutes and using them in a telescopic manner.