Work

Synthesis of Bicyclo[1.1.1]Pentane Z‐Substituted Enamides, Enol Ethers, and Vinyl Sulfides Using Iodine (III) Reagents

Year: 2025

Type: article

Abstract: Bicyclo[1.1.1]pentanes (BCPs) are well‐studied bioisosteres for para ‐substituted benzene rings, and numerous methods for synthesizing 1,3‐difunctionalized BCPs have been developed. However, synthetic approaches to access vinyl BCP motifs remain limited, with only few reports on the synthesis of BCP‐olefins bearing heteroatom substituents. Herein, we present the synthesis of BCP‐substituted enamides, enol ethers, and vinyl sulfides through the sequential functionalization of ethynylbenziodoxolone (EBX) reagents containing a BCP scaffold. Stereoselective addition of a nucleophile generates heteroatomic Z‐vinylbenziodoxolone (VBX) reagents. The hypervalent iodine substituent of the VBX reagents serves then as a versatile platform for further arylation, vinylation, and trifluoromethylation. This method provides a modular synthesis of previously inaccessible heteroatom‐substituted vinyl BCPs.

Source: Angewandte Chemie

DOI: 10.1002/ange.202508404

Authors: Najung Lee, Jonas Dechent, Elija Grinhagena, Jerome Waser

Institution: École Polytechnique Fédérale de Lausanne

Language: English

Topic: Oxidative Organic Chemistry Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,790

Funder: Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung