Issue 5, 2018
From the journal:

Reaction Chemistry & Engineering

Sequential double C–H functionalization of 2,5-norbornadiene in flow†

Heejin Kim, ORCID logo a   Zuoyufan Yin,b   Hidehiro Sakurai ORCID logo *b  and  Jun-ichi Yoshida ORCID logo *ac  

* Corresponding authors

a Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan
E-mail: kim.heejin.2u@kyoto-u.ac.jp

b Division of Applied Chemistry, Graduate School of Engineering, Osaka University, Osaka 565-0871, Japan
E-mail: hsakurai@chem.eng.osaka-u.ac.jp

c National Institute of Technology, Suzuka College, Suzuka, Mie, Japan
E-mail: j-yoshida@jim.suzuka-ct.ac.jp

Abstract

An anionic species of 2,5-norbornadiene was generated and brominated using a flow reactor. In the second step, 2-bromo-2,5-norbornadiene was lithiated with LTMP and reacted with tributyltin chloride. Finally, an integrated one-flow synthesis using various electrophiles was achieved within 3 min to prepare 2-bromo-2,5-norbornadienes bearing a functional group at the 3-position.

Graphical abstract: Sequential double C–H functionalization of 2,5-norbornadiene in flow

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Article information

DOI
https://doi.org/10.1039/C8RE00131F
Article type
Communication
Submitted
18 Jul 2018
Accepted
26 Jul 2018
First published
27 Jul 2018

React. Chem. Eng., 2018,3, 635-639

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Sequential double C–H functionalization of 2,5-norbornadiene in flow

H. Kim, Z. Yin, H. Sakurai and J. Yoshida, React. Chem. Eng., 2018, 3, 635 DOI: 10.1039/C8RE00131F

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