Nitrogen-Nitrogen Radical Coupling-Enabled Precise Difunctionalization of Carbon-Nitrogen Double Bonds

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Photochemistry

Background:

• Carbon-nitrogen double bonds (C═N) are crucial functional groups in organic molecules.
• Efficient difunctionalization of C═N bonds remains a challenge in synthetic chemistry.

Purpose of the Study:

• To develop a novel metal-free strategy for the difunctionalization of C═N bonds.
• To achieve direct radical difunctionalization via nitrogen-nitrogen radical coupling.

Main Methods:

• Utilized a photoinduced energy transfer strategy.
• Employed oxime ester-based bifunctional reagents.
• Investigated radical difunctionalization of C═N bonds.

Main Results:

• Achieved efficient metal-free difunctionalization of C═N bonds.
• Demonstrated direct radical difunctionalization through nitrogen-nitrogen radical coupling.
• Obtained over 35 examples with yields up to 96%.

Conclusions:

• The developed method offers a novel approach for C═N bond difunctionalization.
• The strategy shows broad substrate scope, including biologically relevant molecules.
• This work expands the synthetic utility of heteroatom-containing unsaturated bonds.