Fe(III)/NaBD4-mediated regioselective deuteration/cyclization of 1,7-enynes and 1,7-dienes

Guiling Li; Mengshuang Guo; Yijia Zhang; Xiubin Zhang; Xiaowei Dong; Xiaotong Deng; Zijuan Liang; Zongyuan Su; Zhen Zhang

doi:10.1039/D5CC04107D

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Fe(iii)/NaBD₄-mediated regioselective deuteration/cyclization of 1,7-enynes and 1,7-dienes

Guiling Li,^a Mengshuang Guo,^a Yijia Zhang,^a Xiubin Zhang,^a Xiaowei Dong,^a Xiaotong Deng,^a Zijuan Liang,^a Zongyuan Su^a and Zhen Zhang

*^a

Author affiliations

* Corresponding authors

^a School of Chemistry and Chemical Engineering, Yantai University, Yantai, P. R. China
E-mail: zhangz@ytu.edu.cn

Abstract

We developed an Fe(III)/NaBD₄-mediated method for regioselective deuteration/cyclization of 1,7-enynes and 1,7-dienes, yielding deuterated dihydroquinolin-2(1H)-ones and benzo[b]azepinones. Distinct regioselectivity was observed: deuterium radical addition favors neutral double bonds in enynes (via 6-exo cyclization) and electron-deficient olefins in dienes (via 7-endo cyclization). Isotope studies confirmed water as the carbonyl oxygen source. The protocol's scalability and synthetic compatibility highlight its broad utility.

Download options Please wait...

Supplementary files

Article information

DOI: https://doi.org/10.1039/D5CC04107D
Article type: Communication
Submitted: 21 Jul 2025
Accepted: 05 Sep 2025
First published: 05 Sep 2025

Download Citation

Chem. Commun., 2025, Advance Article

Permissions

Request permissions

Fe(III)/NaBD₄-mediated regioselective deuteration/cyclization of 1,7-enynes and 1,7-dienes

G. Li, M. Guo, Y. Zhang, X. Zhang, X. Dong, X. Deng, Z. Liang, Z. Su and Z. Zhang, Chem. Commun., 2025, Advance Article , DOI: 10.1039/D5CC04107D

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Chemical Communications