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Visible-light-promoted remote C(sp(3))-H amidation and chlorination
1State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China.
Organic Letters
|April 9, 2015
Summary
Visible light promotes remote C(sp(3))-H functionalization of N-chlorosulfonamides (NCSs) for amidation and chlorination. This efficient photocatalytic method yields diverse heterocycles and chlorides, including complex molecules.
Area of Science:
- Organic Chemistry
- Photocatalysis
- Synthetic Methodology
Background:
- C(sp(3))-H functionalization is crucial for synthesizing complex organic molecules.
- Developing efficient and selective methods for remote C(sp(3))-H functionalization remains a significant challenge.
- Visible-light photocatalysis offers a sustainable and mild approach to organic transformations.
Purpose of the Study:
- To report a novel visible-light-promoted method for C(sp(3))-H amidation and chlorination of N-chlorosulfonamides (NCSs).
- To achieve remote C(sp(3))-H functionalization under mild reaction conditions.
- To demonstrate the broad applicability of the method for synthesizing nitrogen-containing heterocycles, chlorides, and functionalizing complex natural product derivatives.
Main Methods:
- Utilizing N-chlorosulfonamides (NCSs) as substrates.
- Employing visible light irradiation in the presence of a photocatalyst (as low as 0.1 mol %).
- Conducting reactions in a weak basic solution at room temperature.
Main Results:
- Successful C(sp(3))-H amidation and chlorination of NCSs were achieved.
- A variety of nitrogen-containing heterocycles were synthesized with up to 94% yield.
- Diverse chlorides were prepared with up to 93% yield.
- Late-stage C(sp(3))-H functionalization of biologically relevant amine derivatives demonstrated excellent yields and regioselectivity.
Conclusions:
- The developed method provides an efficient and versatile route for remote C(sp(3))-H functionalization.
- This photocatalytic approach offers a sustainable and mild alternative for synthesizing valuable organic compounds.
- The methodology shows potential for late-stage functionalization in drug discovery and development.
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