Publication

Synthesis of Csp3 Chlorinated Compounds from Cyclopropanes, Olefins, and C–H Bonds via Photolysis of Willgerodt-Type Reagents

2026

Abstract

Csp 3 −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-, NO 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.

Official source

https://infoscience.epfl.ch/entities/publication/3b8f3b51-e231-4019-8f7f-ff08bf292bf2

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2026

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/3b8f3b51-e231-4019-8f7f-ff08bf292bf2

About this result

Related concepts (32)

Free-radical halogenation

In organic chemistry, free-radical halogenation is a type of halogenation. This chemical reaction is typical of alkanes and alkyl-substituted aromatics under application of UV light. The reaction is used for the industrial synthesis of chloroform (CHCl3), dichloromethane (CH2Cl2), and hexachlorobutadiene. It proceeds by a free-radical chain mechanism. The chain mechanism is as follows, using the chlorination of methane as a usual example: 1. Initiation: Splitting or homolysis of a chlorine molecule to form two chlorine atoms, initiated by ultraviolet radiation .

Chemical synthesis

In chemistry, chemical synthesis (chemical combination) is the artificial execution of chemical reactions to obtain one or several products. This occurs by physical and chemical manipulations usually involving one or more reactions. In modern laboratory uses, the process is reproducible and reliable. A chemical synthesis involves one or more compounds (known as reagents or reactants) that will experience a transformation when subjected to certain conditions. Various reaction types can be applied to formulate a desired product.

Total synthesis

Total synthesis is the complete chemical synthesis of a complex molecule, often a natural product, from simple, commercially-available precursors. It usually refers to a process not involving the aid of biological processes, which distinguishes it from semisynthesis. Syntheses may sometimes conclude at a precursor with further known synthetic pathways to a target molecule, in which case it is known as a formal synthesis. Total synthesis target molecules can be natural products, medicinally-important active ingredients, known intermediates, or molecules of theoretical interest.

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Synthesis of Csp3 Chlorinated Compounds from Cyclopropanes, Olefins, and C–H Bonds via Photolysis of Willgerodt-Type Reagents

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