Synthesis of Sterically Congested Carbonyl Compounds via an <i>ipso</i> -Selective Sulfonium Rearrangement
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 <i>ipso</i>-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.
Authors
- Immo Klose (ORCID: https://orcid.org/0000-0002-9204-2106)
- Christian Knittl‐Frank (ORCID: https://orcid.org/0000-0001-9167-5414)
- Boris Maryasin (ORCID: https://orcid.org/0000-0001-7943-7333)
- Daniel Kaiser (ORCID: https://orcid.org/0000-0001-8895-9969)
- Nuno Maulide (ORCID: https://orcid.org/0000-0003-3643-0718)
- Nicolas G.-Simonian (ORCID: https://orcid.org/0000-0001-8913-9612)
Institutions
- University of Vienna (AT)
Publication Details
- Journal
- Journal of the American Chemical Society
- Published
- 2025-10-08
- DOI
- https://doi.org/10.1021/jacs.5c13777
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 0.00