Work

Suzuki–Miyaura coupling of arylthianthrenium tetrafluoroborate salts under acidic conditions

Year: 2024

Type: article

Abstract: The palladium-catalysed Suzuki–Miyaura cross-coupling (SMC) is currently the most commonly used reaction to construct carbon–carbon bonds in the pharmaceutical industry. Typical methods require the use of a base, which limits the substrate scope. To mitigate this shortcoming, substantial effort has been made to develop base-tolerant organoboron reagents, efficient catalysts and reaction conditions that do not require external bases. Still, many boronic acids cannot be used or must be independently protected, and many Lewis-basic functional groups poison the catalyst. Here we report a conceptually different SMC reaction that can proceed even under acidic conditions, with a broad substrate scope. Key to this advance is the formation of an acid-stable, palladium-based ion pair between the reaction partners that does not require base for subsequent productive transmetallation. Boronic acids that cannot be used directly in other SMC reactions, such as 2-pyridylboronic acid and boronic acids with strong Lewis bases, can now be used successfully.

Source: Nature Synthesis

DOI: 10.1038/s44160-024-00631-4

Authors: Li Zhang, Yuanhao Xie, Zibo Bai, Tobias Ritter

Institutions: Max-Planck-Institut für Kohlenforschung, RWTH Aachen University

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $12,290

Funders: Alexander von Humboldt-Stiftung, Max-Planck-Gesellschaft