Transition Metal‐Driven Selectivity in Direct C−H Arylation of Imidazo[2,1‐b]Thiazole

Transition Metal‐Driven Selectivity in Direct C−H Arylation of Imidazo[2,1‐b]Thiazole

Abstract A selective direct arylation of the different Csp2‐H bonds of imidazo[2,1‐b]thiazole with (hetero) aryl halides can be achieved simply by switching from a palladium catalyst system to the use of stoichiometric amounts of copper. The observed selectivity, also rationalized by DFT calculation...

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Bibliographic Details
Main Authors: Dr. Antonio Del Vecchio, Elisabetta Rosadoni, Lorenzo Ballerini, Dr. Angela Cuzzola, Prof. Filippo Lipparini, Dr. Paolo Ronchi, Dr. Sara Guariento, Dr. Matteo Biagetti, Prof. Marco Lessi, Prof. Fabio Bellina
Format: Article
Language:English
Published: Wiley-VCH 2024-11-01
Series:ChemistryOpen
Subjects:
imidazo[2,1-b]thiazoles
direct C−H arylation
selectivity
palladium catalysis
copper
Online Access:https://doi.org/10.1002/open.202400180
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Summary:Abstract A selective direct arylation of the different Csp2‐H bonds of imidazo[2,1‐b]thiazole with (hetero) aryl halides can be achieved simply by switching from a palladium catalyst system to the use of stoichiometric amounts of copper. The observed selectivity, also rationalized by DFT calculations, can be explained by a change in the mechanistic pathways between electrophilic palladation and base‐promoted C−H metalation.
ISSN:2191-1363

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