Work

Cationic, Iodine(III)‐Mediated and Directed Diastereoselective Oxidation of Inert C−H Bonds in Cyclic Hydrocarbons

Year: 2025

Type: article

Abstract: Over the past three decades, the functionalization of unactivated C-H bonds has become a workhorse of synthesis. In the field of C-H bond oxygenation, most established methods hinge on single-electron reactivity, encountering challenges pertaining to regio- and/or stereocontrol. Herein, we describe a conceptually distinct strategy relying on the unique features of carbocation chemistry. Our iodine(III)-mediated method achieves the diastereoselective oxygenation of remote C-H bonds at traditionally unreactive sites and enables late-stage functionalization at steroidal frameworks as well as an unusual chirality relay.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.202421872

Authors: Nicolas G.‐Simonian, Bogdan R. Brutiu, Daniel Kaiser, Nuno Maulide

Institution: University of Vienna

Language: English

Topic: Oxidative Organic Chemistry Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,510

Funders: Österreichischen Akademie der Wissenschaften, Austrian Science Fund, Universität Wien, H2020 European Research Council