期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2020, 期 5, 页码 618-622出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201901729
关键词
Borylation; Flow microreactors; Lithiation; Piperidylmethyl groups; Cross-coupling
资金
- MEXT [15H05849, 26288049, 26220804, 25220913, 17865428, 2707]
- AMED [18ak0101090h]
- Japan Science and Technology Agency's (JST) A-step program [18067420]
- CREST
- Ogasawara Foundation for the Promotion of Science Engineering
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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