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Updated: Aug 18, 2025

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

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Published on: July 28, 2018

Selectfluor®-enabled photochemical selective C(sp³)-H(sulfonyl)amidation.

Yuehua Chen¹, Boxuan Yang¹, Qian-Yu Li¹

¹Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China. gongl@xmu.edu.cn.

Chemical Communications (Cambridge, England)

|December 8, 2022

Summary

This summary is machine-generated.

New C(sp3)-H (sulfonyl)amidation reactions avoid transition metals and photosensitizers. Selectfluor® acts as a photoactive component, HAT precursor, and oxidant for efficient N-functionalization under mild conditions.

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Area of Science:

Organic Chemistry
Synthetic Chemistry
Methodology Development

Background:

C(sp3)-H functionalization is crucial for molecule synthesis.
Existing methods often rely on transition metals or photosensitizers.
Developing metal- and photosensitizer-free methods is highly desirable.

Purpose of the Study:

To develop a novel transition metal- and photosensitizer-free method for C(sp3)-H (sulfonyl)amidation.
To utilize Selectfluor® as a multifunctional reagent in this transformation.
To demonstrate the broad applicability of the developed method.

Main Methods:

Employing Selectfluor® as a photoactive component, hydrogen atom transfer (HAT) precursor, and oxidant.
Utilizing mild reaction conditions.
Investigating the reaction scope with various substrates.

Main Results:

Successful realization of transition metal- and photosensitizer-free C(sp3)-H (sulfonyl)amidation.
Good yields and high chemo- and site-selectivity achieved.
Demonstrated applicability to toluene derivatives, cycloalkanes, natural products, and bioactive molecules.

Conclusions:

Selectfluor® is a versatile reagent for metal- and photosensitizer-free C(sp3)-H (sulfonyl)amidation.
The developed method offers a mild, efficient, and selective route to N-containing products.
This approach expands the toolkit for C(sp3)-H functionalization in organic synthesis.