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Nickel-Catalyzed cine-Substitution Toward Carbonyl Dance
Eito Moriya1, Kei Muto2, Junichiro Yamaguchi1
1Department of Applied Chemistry, Waseda University, 513, Wasedatsurumakicho, Shinjuku, Tokyo, 162-0041, Japan.
Chemistry, an Asian Journal
|January 14, 2026
Summary
This study introduces a nickel-catalyzed cine-substitution for 1,2-carbonyl translocation in tetralones. The reaction efficiently converts tetralones into β-tetralones using various nucleophiles, expanding carbonyl migration chemistry.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Functional group positional exchange is key for organic molecule diversification.
- Carbonyl migration reactions are valuable synthetic tools.
Purpose of the Study:
- To develop a nickel-catalyzed cine-substitution for 1,2-carbonyl translocation (carbonyl dance) in tetralone derivatives.
- To expand the scope of carbonyl migration chemistry.
Main Methods:
- Nickel-catalyzed cine-substitution using Ni(dcype)(CO)2 and K3PO4.
- Reaction of tetralone derivatives with various amines and heteroatom nucleophiles.
- Hydrolysis of intermediate enamines to yield β-tetralones.
- Development of a one-pot protocol for sequential transformations.
Main Results:
- Achieved 1,2-carbonyl translocation in tetralone derivatives with high yields and regioselectivity.
- Demonstrated tolerance for diverse nucleophiles, including secondary anilines, phenoxazine, and hindered alcohols.
- Established a one-pot protocol yielding β-tetralones or tertiary amines.
Conclusions:
- The reported nickel-catalyzed cine-substitution provides a new platform for functional group transposition.
- This method expands the utility of carbonyl migration chemistry.
- The reaction offers a versatile approach to structurally diverse β-tetralones and related compounds.
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