A Synthetic Approach to Dimetalated Arenes Using Flow Microreactors and the Switchable Application to Chemoselective Cross-Coupling Reactions
Yosuke Ashikari, Tomoko Kawaguchi, Kyoko Mandai, Yoko Aizawa, Aiichiro Nagaki
Abstract
In spite of their potential utility, the chemistry of dimetalated arenes is still in its infancy because they are extremely difficult to synthesize. We report a novel method of synthesizing arenes bearing a boryl group and a metallic substituent, such as boryl, silyl, stannyl, or zincyl groups, in an integrated flow microreactor based on the generation and reactions of aryllithiums bearing a trialkyl borate moiety. The bimetallic arenes showed a remarkable chemoselectivity in palladium-catalyzed cross-coupling reactions. The selectivity was switched by the selection of the metal species that constitutes the dimetalated arenes as well as appropriate catalysts.
Topics & Concepts
ChemistryChemoselectivityMicroreactorBimetallic stripMoietySilylationSubstituentSelectivityPalladiumFlow chemistryCombinatorial chemistryCoupling reactionCatalysisOrganic chemistryCatalytic Cross-Coupling ReactionsInnovative Microfluidic and Catalytic Techniques InnovationRadical Photochemical Reactions