Light-induced gold-catalyzed Hiyama arylation

• Verfasst von: Xie, Jin [VerfasserIn]
• Verfasst von: Sekine, Kohei [VerfasserIn]
• Verfasst von: Witzel, Sina [VerfasserIn]
• Verfasst von: Krämer, Petra [VerfasserIn]
• Verfasst von: Rudolph, Matthias [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Titel: Light-induced gold-catalyzed Hiyama arylation
• Titelzusatz: a coupling access to biarylboronates
• Verf.angabe: Jin Xie, Kohei Sekine, Sina Witzel, Petra Krämer, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi
• Umfang: 6 S.
• Fussnoten: Gesehen am 05.02.2019
• Titel Quelle: Enthalten in: Angewandte Chemie / International edition
• Jahr Quelle: 2018
• Band/Heft Quelle: 57(2018), 51, S. 16648-16653
• ISSN Quelle: 1521-3773
• DOI: doi:10.1002/anie.201806427
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 1587274515

Abstract

Organoboron compounds are versatile synthetic building blocks. We herein report a new strategy, a photochemical gold-catalyzed chemo-selective Hiyama arylation of B,Si bifunctionalized reagents with diazonium salts, which is orthogonal to common strategies and therefore a unique tool for synthesis of valuable biarylboronates. With this new methodology a wide array of diversely functionalized sp2- and sp3-hybridized biarylboronates were obtained. Notably, the synergism of gold catalysis with copper catalysis or palladium catalysis, allows for one-pot iterative C−X (heteroatom) and C−C couplings for the rapid assembly of several simple fragments to relatively complex molecules. Mechanistic studies indicated that photosensitizer-free conditions were superior to gold/Ru(bpy)3Cl2 dual catalysis.