Dearomative triple elementalization of quinolines driven by visible light

Shiho Ishigaki, Yuki Nagashima (), Daiki Yukimori, Jin Tanaka, Takashi Matsumoto, Kazunori Miyamoto, Masanobu Uchiyama () and Ken Tanaka ()
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Shiho Ishigaki: Tokyo Institute of Technology, O-okayama, Meguro-ku
Yuki Nagashima: Tokyo Institute of Technology, O-okayama, Meguro-ku
Daiki Yukimori: The University of Tokyo
Jin Tanaka: Tokyo Institute of Technology, O-okayama, Meguro-ku
Takashi Matsumoto: Rigaku Corporation
Kazunori Miyamoto: The University of Tokyo
Masanobu Uchiyama: The University of Tokyo
Ken Tanaka: Tokyo Institute of Technology, O-okayama, Meguro-ku

Nature Communications, 2023, vol. 14, issue 1, 1-11

Abstract: Abstract Organoboron and organosilicon compounds are used not only as synthetic building blocks but also as functional materials and pharmaceuticals, and compounds with multiple boryl and silyl groups are beginning to be used for these purposes. Especially in drug discovery, methodology providing easy stereoselective access to aliphatic nitrogen heterocycles bearing multiple boryl or silyl groups from readily available aromatic nitrogen heterocycles would be attractive. However, such transformations remain challenging, and available reactions have been mostly limited to dearomative hydroboration or hydrosilylation reactions. Here, we report the dearomative triple elementalization (carbo-sila-boration) of quinolines via the addition of organolithium followed by photo-boosted silaboration, affording the desired products with complete chemo-, regio-, and stereoselectivity. The reaction proceeds via the formation of silyl radicals instead of silyl anions. We also present preliminary studies to illustrate the potential of silaboration products as synthetic platforms.

Date: 2023
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DOI: 10.1038/s41467-023-36161-4

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