Publication

Playing with Electrons to Activate Strained Rings

2026

Abstract

Strained ring systems offer unique opportunities for C-C single bond activation. In this presentation, I will present three different fundamental approaches for ring-opening: heterolytic cleavage, single electron transfer and homolytic cleavage. Each strategy will be illustrated by one recent example from our research group: 1) Heterolytic cleavage: Silylium-catalyzed (4+2) annulation of indoles and aminocyclobutanes and application in the formal total synthesis of Strictamine (Angew. Chem.. Int. Ed. 2023, e202302420 and Helv. Chim. Acta. 2026, e202500163) 2) Single electron transfer: Oxidative ring opening of cyclopropanes using hypervalent iodine reagents (Chem. Sci. 2022, 12831 and JACS Au 2026, 10.1021/jacsau.5c01226) 3) Homolytic cleavage: Energy-transfer photocatalyzed ring opening reactions of cyclopropanes (JACS 2023, 25411 and Angew. Chem., Int. Ed. 2024, e202417719)

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https://infoscience.epfl.ch/entities/publication/0cb7a4e3-0020-4b39-87c0-702f9206671f

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2026

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/0cb7a4e3-0020-4b39-87c0-702f9206671f

About this result

Related concepts (13)

Homolysis (chemistry)

In chemistry, homolysis () or homolytic fission is the dissociation of a molecular bond by a process where each of the fragments (an atom or molecule) retains one of the originally bonded electrons. During homolytic fission of a neutral molecule with an even number of electrons, two free radicals will be generated. That is, the two electrons involved in the original bond are distributed between the two fragment species. Bond cleavage is also possible by a process called heterolysis.

Carbon–hydrogen bond

In chemistry, the carbon-hydrogen bond ( bond) is a chemical bond between carbon and hydrogen atoms that can be found in many organic compounds. This bond is a covalent, single bond, meaning that carbon shares its outer valence electrons with up to four hydrogens. This completes both of their outer shells, making them stable. Carbon–hydrogen bonds have a bond length of about 1.09 Å (1.09 × 10−10 m) and a bond energy of about 413 kJ/mol (see table below). Using Pauling's scale—C (2.55) and H (2.

Carbon–carbon bond

A carbon–carbon bond is a covalent bond between two carbon atoms. The most common form is the single bond: a bond composed of two electrons, one from each of the two atoms. The carbon–carbon single bond is a sigma bond and is formed between one hybridized orbital from each of the carbon atoms. In ethane, the orbitals are sp3-hybridized orbitals, but single bonds formed between carbon atoms with other hybridizations do occur (e.g. sp2 to sp2). In fact, the carbon atoms in the single bond need not be of the same hybridization.

Related publications (3)

Playing with Electrons to Activate Strained Rings

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