Light-Induced Gold-Catalyzed Hiyama Arylation: A Coupling Access to Biarylboronates
Jin Xie1, Kohei Sekine2, Sina Witzel2
1State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, P. R. China.
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)3 Cl2 dual catalysis.
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