Work

Synthesis of Sterically Congested Carbonyl Compounds via an ipso -Selective Sulfonium Rearrangement

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide Despite the success of metal-catalyzed cross-coupling strategies to assemble a variety of C–C bonds, the synthesis of sterically congested α-arylated carbonyl compounds remains a difficult task. Herein, we present an ipso -rearrangement approach relying on electron redistribution in sulfonium intermediates. This modular method enables the synthesis of a variety of α-arylated carbonyl compounds and is orthogonal to traditional metal-catalyzed cross-coupling strategies. More importantly, it demonstrated remarkable robustness toward steric hindrance and allowed us to efficiently forge congested C–C bonds.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.5c13777

Authors: Immo Klose, Christian Knittl-Frank, Nicolas G.-Simonian, Boris Maryasin, Daniel Kaiser, Nuno Maulide

Institution: University of Vienna

Language: English

Topic: Sulfur-Based Synthesis Techniques

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500