What question did this study set out to answer?

This research focuses on developing a method for synthesizing 2-aminotetralins while minimizing side reactions.

July 2, 2026Advanced Synthesis & Catalysis0 citationsOpen Access

Synthesis of 2‐Aminotetralins via Pd‐Catalyzed Alkene Difunctionalization Reactions: Use of Ligand Structure to Suppress Facile Intramolecular 5‐ Exo‐ Heck Reactions

ACAndrew CruzUniversity of Michigan JWJohn P. WolfeUniversity of Michigan

Key Points

This research focuses on developing a method for synthesizing 2-aminotetralins while minimizing side reactions.
Utilized palladium-catalyzed coupling reactions with 2-(but-3-en-1-yl)phenyl triflates and amine nucleophiles.
Employed t BuPhCPhos ligand to suppress competing intramolecular Heck reactions.
Analyzed the impact of substrate substituents and ligand structure on reaction outcomes.
Achieved moderate to good yields of 2-amino tetralins and 1-aminomethyl indanes.
Maintained diastereoselectivities ranging from 5:1 to > 20:1.
Effectively suppressed the intramolecular Heck reaction using the specified ligand.

Abstract

The palladium‐catalyzed coupling of 2‐(but‐3‐en‐1‐yl)phenyl triflates with amine nucleophiles affords separable mixtures of 2‐amino tetralins and 1‐aminomethyl indanes in moderate to good yields. The competing intramolecular Heck arylation of the starting materials can be effectively suppressed through the use of t BuPhCPhos as the ligand for palladium. Transformations of substrates bearing substituents on the alkyl chain proceed with diasteroselectivities from 5:1 to > 20:1. The scope, limitations, mechanism, and stereocontrol are discussed, along with the influence of ligand structure on reaction outcome.

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