Bench-stable sulfoxide-based boronates: preparation and application in a tandem Suzuki reaction

0501726 - FZÚ 2019 RIV DE eng J - Journal Article
Čubiňák, M. - Eigner, Václav - Tobrman, T.
Bench-stable sulfoxide-based boronates: preparation and application in a tandem Suzuki reaction.
Advanced Synthesis & Catalysis. Roč. 360, č. 23 (2018), s. 4604-4614. ISSN 1615-4150. E-ISSN 1615-4169
Institutional support: RVO:68378271
Keywords : palladium * biaryls * Suzuki-Miyaura reaction * cross-coupling * boron
OECD category: Condensed matter physics (including formerly solid state physics, supercond.)
Impact factor: 5.451, year: 2018

A set of novel aromatic and heteroaromatic bench-stable sulfoxide-based boronates was prepared. The structure of the boronates was established by means of X-ray crystallography, and the prepared boronates were successively used in Suzuki cross-coupling reactions under different conditions. We also developed a tandem Suzuki reaction so that a base is generated during the nucleophilic addition of Grignard reagents to 4-bromobenzaldehyde. The formed intermediates were smoothly coupled with the prepared boronates and the boronic acids under external base-free conditions.
Permanent Link: http://hdl.handle.net/11104/0293723