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Related Experiment Video

Updated: Jun 5, 2025

Ethylene Polymerizations Using Parallel Pressure Reactors and a Kinetic Analysis of Chain Transfer Polymerization

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Published on: November 27, 2015

Selective Ni(I)/Ni(III) Process for Consecutive Geminal C(sp³)-C(sp²) Bond Formation.

Xuejiao Li¹, Yu Gan¹, Yi-Yang Wang¹

¹School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China.

Journal of the American Chemical Society

|December 13, 2024

Summary

This study introduces a novel nickel-catalyzed reaction that efficiently forms two new carbon-carbon bonds in one step. This method rapidly assembles complex molecules from simple starting materials, useful for drug discovery.

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Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Multicomponent cross-couplings offer efficient molecular construction.
Selective formation of multiple bonds, especially in cross-electrophile coupling, is challenging.

Purpose of the Study:

To develop a novel nickel-catalyzed method for forming two geminal C(sp3)-C(sp2) bonds.
To enable the synthesis of complex molecular architectures from simple precursors.

Main Methods:

Consecutive open-shell reductive nickel catalysis.
Utilized zirconaaziridine and elemental Mg0 as reductants.
Employed C(sp2)-I reactants and a methylene electrophile.

Main Results:

Successfully formed two geminal C(sp3)-C(sp2) bonds from similar C(sp2)-I reactants.
Demonstrated broad applicability with various (hetero)aromatic, alkenyl, and glycal halides.
Achieved rapid assembly of medicinally relevant scaffolds with high functional group tolerance.

Conclusions:

The developed protocol provides a powerful strategy for complex molecule synthesis.
Kinetic studies suggest a dual "sequential reduction" catalytic pathway.
High selectivity was observed in key catalytic steps, including oxidative addition and halide abstraction.