NADH Analogues Enable Metal- and Light-Free Decarboxylative Functionalization.
Lei Liang1,2, Yue-Hui Wang1, Cheng-Xing Cui1
1School of Chemistry and Chemical Engineering, Henan Institute of Science and Technology Hualan Avenue East Section, Xinxiang, Henan Province, 453007, China E-mails.
Angewandte Chemie (International Ed. in English)
|November 25, 2024
Summary
This study introduces a rapid, metal- and light-free method for decarboxylative functionalization using reduced nicotinamide adenine dinucleotide (NADH) analogues. The approach enables diverse bond formation and streamlines the synthesis of valuable sp3 carbon-enriched compounds.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Decarboxylative reactions are crucial in organic synthesis.
- Metal- and light-mediated methods often present limitations.
- Developing efficient, metal-free alternatives is highly desirable.
Purpose of the Study:
- To develop a novel metal- and light-free decarboxylative functionalization strategy.
- To enable efficient bond formation using reduced nicotinamide adenine dinucleotide (NADH) analogues.
- To streamline the synthesis of sp3 carbon-enriched compounds.
Main Methods:
- Utilized reduced nicotinamide adenine dinucleotide (NADH) analogues.
- Employed in situ preparation of aryliodine(III) dicarboxylates.
- Conducted reactions under open-air and ambient conditions within 5 minutes.
Main Results:
- Achieved efficient and operationally simple decarboxylative functionalization.
- Demonstrated a broad substrate scope with over 70 examples.
- Successfully applied the method for late-stage functionalization of drug molecules and natural products.
- Elucidated the mechanistic pathway through experimental and computational studies.
Conclusions:
- The developed method offers a new dimension to classical decarboxylative reactions.
- Provides a streamlined synthesis for sp3 carbon-enriched compounds.
- Highlights the synthetic utility and broad applicability of the novel approach.
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