Issue 66, 2019
From the journal:

Chemical Communications

Iridium-catalyzed alkenyl C–H allylation using conjugated dienes†

Liangyao Xu,a   Keke Meng,a   Jian Zhang, ORCID logo *a   Yaling Sun,a   Xiunan Lu,a   Tingyan Li,a   Yan Jianga  and  Guofu Zhong*a  

* Corresponding authors

a College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, China
E-mail: zhangjian@hznu.edu.cn, zgf@hznu.edu.cn

Abstract

An iridium-catalyzed C–H allylation of acrylamides with conjugated dienes was developed, using NH-Ts amide as the directing group. The ligand- and additive-free protocol provided a convenient and atom economic synthesis of branched 1,4-diene skeletons, enabling the tolerance of a wide scope of functionalities such as OMe, F, Cl, Br and CF3. The utility of this protocol is also demonstrated by a preparative scale, as well as C–H functionalization of artemisic amide. Furthermore, NH-Ts amide was efficiently removed by methylation and hydrolysis procedures to provide 1,4-dienoic acid.

Graphical abstract: Iridium-catalyzed alkenyl C–H allylation using conjugated dienes

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Article information

DOI
https://doi.org/10.1039/C9CC04419A
Article type
Communication
Submitted
09 Jun 2019
Accepted
18 Jul 2019
First published
29 Jul 2019

Chem. Commun., 2019,55, 9757-9760

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Iridium-catalyzed alkenyl C–H allylation using conjugated dienes

L. Xu, K. Meng, J. Zhang, Y. Sun, X. Lu, T. Li, Y. Jiang and G. Zhong, Chem. Commun., 2019, 55, 9757 DOI: 10.1039/C9CC04419A

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