What the study found
The study found that palladium-catalyzed coupling of 2-(but-3-en-1-yl)phenyl triflates with amine nucleophiles gives separable mixtures of 2-amino tetralins and 1-aminomethyl indanes in moderate to good yields. It also found that the ligand t BuPhCPhos can effectively suppress a competing intramolecular Heck arylation reaction.
Why the authors say this matters
The authors state that the work discusses scope, limitations, mechanism, stereocontrol, and the influence of ligand structure on reaction outcome. The study suggests that ligand choice is important for controlling this palladium-catalyzed alkene difunctionalization reaction.
What the researchers tested
The researchers tested palladium-catalyzed coupling reactions between 2-(but-3-en-1-yl)phenyl triflates and amine nucleophiles. They also examined substrates with substituents on the alkyl chain, and they compared how ligand structure affected the reaction, including suppression of the competing intramolecular 5-exo-Heck reaction.
What worked and what didn't
The coupling reactions produced separable mixtures of the two product types in moderate to good yields. Use of t BuPhCPhos as the palladium ligand effectively suppressed the competing intramolecular Heck arylation of the starting materials. For substrates with alkyl-chain substituents, the reactions gave diastereoselectivities from 5:1 to greater than 20:1.
What to keep in mind
The abstract does not provide detailed data for individual substrates, so the full scope is not specified here. It also notes limitations and mechanism are discussed in the paper, but those details are not included in the abstract summary.
Key points
- Palladium-catalyzed coupling of 2-(but-3-en-1-yl)phenyl triflates with amine nucleophiles yielded 2-amino tetralins and 1-aminomethyl indanes.
- t BuPhCPhos was reported to suppress a competing intramolecular Heck arylation reaction.
- The reactions gave moderate to good yields overall.
- Substituted alkyl-chain substrates showed diastereoselectivities from 5:1 to greater than 20:1.
- The authors discuss scope, limitations, mechanism, stereocontrol, and ligand effects.
Disclosure
- Research title:
- Palladium ligand choice suppresses competing indane formation
- Authors:
- Andrew Cruz, John P. Wolfe
- Institutions:
- University of Michigan, University of Michigan
- Publication date:
- 2026-06-30
- DOI:
- 10.1002/adsc.70544
- OpenAlex record:
- View
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