ArticleChemistry (Weinheim an der Bergstrasse, Germany)2019
Enantioselective C2-Alkylation of Indoles through a Redox-Relay Heck Reaction of 2-Indole Triflates.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Homologation of aryl ketones to long-chain ketones and aldehydes via C-C bond cleavage.iScience · 2022Article
- Stereoselective Remote Functionalization via Palladium-Catalyzed Redox-Relay Heck Methodologies.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- Polarclean/Water as a Safe and Recoverable Medium for Selective C2-Arylation of Indoles Catalyzed by Pd/C.ACS sustainable chemistry & engineering · 2020Article
- Development and Mechanistic Interrogation of Interrupted Chain-Walking in the Enantioselective Relay Heck Reaction.Journal of the American Chemical Society · 2020Article
- Enantioselective Synthesis of Alkyl Allyl Ethers via Palladium-Catalyzed Redox-Relay Heck Alkenylation ofIsrael journal of chemistry · 2020Article
- Enantioselective Synthesis of γ-Functionalized Cyclopentenones and δ-Functionalized Cycloheptenones Utilizing a Redox-Relay Heck Strategy.Advanced synthesis & catalysis · 2020Article
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Authors and funding
3 authors.
Funding
Abstract
A palladium-catalyzed enantioselective redox-relay Heck reaction of 2-indole triflates and disubstituted alkenes is reported. This process combines readily available indole triflates with a variety of alkenes to afford a range of indole derivatives bearing a stereocenter adjacent to C2. Enantioselectivity is achieved through use of a simple pyridine-oxazoline ligand. Tuning the electronics of the indole, through judicious choice of N-protecting group, is required to ensure selective β-hydride elimination away from the indole core. Utility of this method is highlighted in a modular formal synthesis of an S1P
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