A Synthetic Approach to Dimetalated Arenes Using Flow Microreactors and the Switchable Application to Chemoselective Cross-Coupling Reactions

Autor:	Yosuke Ashikari, Yoko Aizawa, Aiichiro Nagaki, Kyoko Mandai, Tomoko Kawaguchi
Rok vydání:	2020
Předmět:	Colloid and Surface Chemistry Flow (mathematics) Chemistry General Chemistry Microreactor 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Catalysis Coupling reaction 0104 chemical sciences
Zdroj:	Journal of the American Chemical Society. 142:17039-17047
ISSN:	1520-5126 0002-7863
DOI:	10.1021/jacs.0c06370
Popis:	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.
Databáze:	OpenAIRE
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