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Updated: Jan 17, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Fe(III)/NaBD4-mediated regioselective deuteration/cyclization of 1,7-enynes and 1,7-dienes
Guiling Li1, Mengshuang Guo1, Yijia Zhang1
1School of Chemistry and Chemical Engineering, Yantai University, Yantai, 264005, P. R. China. 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.
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