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Quadruple Role of Pd Catalyst in Domino Reaction Involving Aryl to Alkyl 1,5‐Pd Migration to Access 1,9‐Bridged Triptycenes
- Source :
- Chemistry – A European Journal. 27:11548-11553
- Publication Year :
- 2021
- Publisher :
- Wiley, 2021.
-
Abstract
- A Pd-catalyzed domino reaction of 1,8,13-tribromo-9-methoxytriptycenes is reported. Under conventional Suzuki coupling conditions, the triptycenes underwent multiple transformations to give 1,9-bridged triptycenes. Based on mechanistic investigations, a single Pd catalyst functions as Pd0 , PdII and PdIV species to catalyze four distinct processes: (1) aryl to alkyl 1,5-Pd migration, (2) intramolecular arylation, (3) homocoupling of phenylboronic acid and (4) Suzuki coupling. DFT calculations revealed that 1,5-Pd migration likely proceeds via both concerted PdII and stepwise PdIV routes. Asymmetric synthesis of the chiral triptycenes, as well as optical resolution, and further transformation are also reported.
Details
- ISSN :
- 15213765 and 09476539
- Volume :
- 27
- Database :
- OpenAIRE
- Journal :
- Chemistry – A European Journal
- Accession number :
- edsair.doi.dedup.....8ca77d07bd24ae6f2a0243a0586efa47
- Full Text :
- https://doi.org/10.1002/chem.202101728