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NiH-catalyzed dearomative hydroalkylation of indoles
Kai Liu1, Yu-Feng Song1, Yang Gao1
1College of Chemical Engineering, State Key Laboratory Breeding Base of Green-Chemical Synthesis Technology, Zhejiang University of Technology, Chaowang Road 18#, Hangzhou 310014, China. yxjia@zjut.edu.cn.
Chemical Communications (Cambridge, England)
|April 27, 2022
Summary
A new nickel-catalyzed reaction enables the synthesis of C2-alkylated indolines from indoles. This method is useful for creating complex drug molecules through late-stage functionalization.
Area of Science:
- Organic Chemistry
- Catalysis
- Medicinal Chemistry
Background:
- Indoles are a crucial heterocyclic motif found in numerous pharmaceuticals.
- Developing efficient methods for indole functionalization is vital for drug discovery.
- Dearomative reactions offer unique pathways to complex molecular architectures.
Purpose of the Study:
- To develop a novel nickel-catalyzed intermolecular dearomative hydroalkylation of indoles.
- To synthesize structurally diverse C2-alkylated indolines.
- To demonstrate the utility of this method for late-stage functionalization of complex molecules.
Main Methods:
- Nickel-catalyzed intermolecular dearomative hydroalkylation reaction.
- Utilized indoles as starting materials.
- Employed various alkylating agents.
Main Results:
- Successfully synthesized a range of C2-alkylated indolines.
- Achieved moderate to excellent yields for the target compounds.
- Demonstrated good functional group tolerance of the developed protocol.
Conclusions:
- A new NiH-catalyzed dearomative hydroalkylation of indoles has been established.
- The protocol provides access to valuable C2-alkylated indoline scaffolds.
- This method holds promise for the synthesis of complex drug candidates.