Synthesis of Biaryls Having a Piperidylmethyl Group Based on Space Integration of Lithiation, Borylation, and Suzuki–Miyaura Coupling

Takahashi, Y.; Ashikari, Y.; Takumi, M.; Shimizu, Y.; Jiang, Y.; Higuma, R.; Ishikawa, S.; Sakaue, H.; Shite, I.; Maekawa, K.; Aizawa, Y.; Yamashita, H.; Yonekura, Y.; Colella, M.; Luisi, R.; Takegawa, T.; Fujita, C.; Nagaki, A.

doi:10.1002/ejoc.201901729

In a flow microreactor, aryllithiums bearing a piperidylmethyl group were generated using nBuLi by precise residence time control and effective temperature control, and then selectively borylated with boronic esters such as 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (BpinOiPr) and trimethyl borate B(OMe)3 by fast mixing. Moreover, the direct integration with Suzuki–Miyaura cross coupling were successfully achieved to obtain nitrogen-containing biaryl compounds. The present method could be applied for the straightforward synthesis of the key intermediate of a bioactive component bearing a piperidylmethyl-biphenyl framework.

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Titolo:	Synthesis of Biaryls Having a Piperidylmethyl Group Based on Space Integration of Lithiation, Borylation, and Suzuki–Miyaura Coupling
Autori:	Takahashi Y. Ashikari Y. Takumi M. Shimizu Y. Jiang Y. Higuma R. Ishikawa S. Sakaue H. Shite I. Maekawa K. Aizawa Y. Yamashita H. Yonekura Y. COLELLA, MARCO LUISI, Renzo Takegawa T. Fujita C. Nagaki A. mostra contributor esterni nascondi contributor esterni
Data di pubblicazione:	2020
Rivista:	EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Handle:	http://hdl.handle.net/11586/268774
Appare nelle tipologie:	1.1 Articolo in rivista

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