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- Title
Synthesis of Biaryls Having a Piperidylmethyl Group Based on Space Integration of Lithiation, Borylation, and Suzuki–Miyaura Coupling.
- Authors
Takahashi, Yusuke; Ashikari, Yosuke; Takumi, Masahiro; Shimizu, Yutaka; Jiang, Yiyuan; Higuma, Ryosuke; Ishikawa, Susumu; Sakaue, Hodaka; Shite, Ibuki; Maekawa, Kei; Aizawa, Yoko; Yamashita, Hiroki; Yonekura, Yuya; Colella, Marco; Luisi, Renzo; Takegawa, Toshihiro; Fujita, Chiemi; Nagaki, Aiichiro
- Abstract
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.
- Subjects
BORYLATION; LITHIATION; SPACE groups; TEMPERATURE control; BORONIC esters; BIPHENYL compounds
- Publication
European Journal of Organic Chemistry, 2020, Vol 2020, Issue 5, p618
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201901729