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Multimodal Precise Control Over Multiselective Carbonylation of 1,3-Enynes
Chang-Sheng Kuai1,2, Yuanrui Wang1,2, Ting Yang1
1Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning 116023, China.
Journal of the American Chemical Society
|February 19, 2025
Summary
This study introduces a new catalytic method for precisely controlling reactions in complex organic molecules. The multimodal strategy enables five selective carbonylations and sequential reactions of 1,3-enynes, advancing synthetic chemistry.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Chemistry
Background:
- Selective catalytic functionalization is key for complex molecule synthesis.
- Controlling multiple reactive sites in multisite substrates is challenging.
- Previous work focused on single- and dual-selective transformations.
Purpose of the Study:
- To develop a multimodal strategy for selective carbonylation of 1,3-enynes.
- To achieve precise control over regio- and stereoselectivity in complex transformations.
- To enable tandem reactions for efficient molecule construction.
Main Methods:
- Fine-tuning catalytic conditions for multimodal transformations.
- Utilizing 1,3-enynes as versatile multisite substrates.
- Conducting mechanistic studies to understand reaction pathways.
Main Results:
- Achieved five distinct regio- and stereoselective carbonylative transformations of 1,3-enynes.
- Demonstrated direct functionalization (1,2- and 2,1-hydroaminocarbonylation).
- Enabled tandem cyclization pathways (2,4-, 1,3-, and 2,3-carbonylation) and up to three sequential reactions with high accuracy.
Conclusions:
- The unified platform offers a robust framework for selectivity control in multisite substrates.
- Broadened the accessible chemical space through 1,3-enyne transformations.
- Exemplified atom- and step-economic principles for drug discovery and materials science.
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