Synthesis of C sp 3 Chlorinated Compounds from Cyclopropanes, Olefins, and C–H Bonds via Photolysis of Willgerodt-Type Reagents

JACS Au 2026 Open access

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Authors: Tin V. T. Nguyen, Tin V. T. Nguyen, Thanh V. Q. Nguyen, Thanh V. Q. Nguyen, Trinh T. H. Tran, Qui-Hien Nguyen, Jérôme Waser
DOI: 10.1021/jacsau.5c01226
Cited by: 3
References: 87

Abstract

-Cl bonds are essential as diversification handles in organic synthesis and are found in many natural products and bioactive molecules. In this work, we introduce a general protocol for the selective chlorination of aryl cyclopropanes, olefins, and activated C-H bonds using direct photoexcitation of Willgerodt-type reagents to generate chlorine radicals. Preliminary results for an iodine-(I/III) catalytic process starting from abundant chloride salts are also presented. Furthermore, a one-pot protocol has been developed for the telescoped functionalization of benzylic chlorides with C-, N-, O-, and S-nucleophiles. Especially, this approach provides a platform to access 1,1-diaryl motifs, which are important building blocks for the synthesis of pharmacophores.

Fields of Study & Subjects

Catalytic C–H Functionalization Methods Radical Photochemical Reactions Synthesis and Reactivity of Sulfur-Containing Compounds

Publication details

Journal / source
JACS Au
Publisher
American Chemical Society (ACS)
Volume
6
Issue
1
Pages
290–298
Publication date
12 January 2026
Language
EN