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Nickel-Catalyzed Switchable Site-Selective Alkene Hydroalkylation by Temperature Regulation.

Jia-Wang Wang¹, De-Guang Liu¹, Zhe Chang¹

¹School of Chemistry and Materials Science, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, University of Science and Technology of China, Hefei, 230026, China.

Angewandte Chemie (International Ed. in English)

|May 24, 2022

Summary

This study introduces a nickel-catalyzed method for alkene hydroalkylation, enabling the synthesis of both alpha- and beta-branched amines from the same starting material by controlling reaction temperature. This provides access to valuable amine building blocks for chemistry and biochemistry.

Keywords:

Asymmetric Catalysis Chain-Walking Cross-Coupling Hydroalkylation Nickel

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Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Regiodivergent functionalization of alkenes is crucial for synthesizing diverse chemical structures.
Developing methods for selective alkene transformations using readily available starting materials remains a key challenge.

Purpose of the Study:

To report a nickel-catalyzed switchable site-selective alkene hydroalkylation protocol.
To enable the synthesis of both alpha- and beta-branched amines from a single alkene substrate.
To explore the potential for catalytic asymmetric synthesis of enantioenriched amines.

Main Methods:

Nickel-catalyzed hydroalkylation of alkenes.
Control of reaction temperature to switch site-selectivity.
Application of a catalytic asymmetric variant for enantioselective synthesis.

Main Results:

Achieved regiodivergent synthesis of alpha- and beta-branched protected amines.
Demonstrated the ability to obtain either regioisomer from the same alkene precursor.
Successfully synthesized enantioenriched beta-branched alkylamines via asymmetric catalysis.

Conclusions:

The developed protocol offers a versatile route to valuable amine building blocks.
Temperature control is key to achieving switchable site-selectivity in nickel-catalyzed alkene hydroalkylation.
The methodology holds promise for applications in pharmaceutical chemistry and biochemistry.