Computational study on palladium-catalyzed alkenylation of remote δ-C(sp3)–H bonds with alkynes: a new understanding of mechanistic insight and origins of site-selectivity

Hui-Min Yan; Ye Tian; Niu Li; Rong Chang; Zhu-Xia Zhang; Xiao-Yun Zhang; Wen-Jing Yang; Zhen Guo; Yan-Rong Li

doi:10.1039/C8RA06077K

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Computational study on palladium-catalyzed alkenylation of remote δ-C(sp³)–H bonds with alkynes: a new understanding of mechanistic insight and origins of site-selectivity†

Hui-Min Yan,^a Ye Tian,^a Niu Li,^a Rong Chang,^a Zhu-Xia Zhang,

^a Xiao-Yun Zhang,^a Wen-Jing Yang,^a Zhen Guo

*^a and Yan-Rong Li*^b

Author affiliations

* Corresponding authors

^a College of Material Science & Engineering, Key Laboratory of Interface Science and Engineering in Advanced Materials, Ministry of Education, Taiyuan University of Technology, Shanxi, P. R. China
E-mail: guozhen@tyut.edu.cn

^b Department of Earth Science and Engineering, Taiyuan University of Technology, Shanxi 030024, P. R. China
E-mail: li.dennis@hotmail.com

Abstract

Palladium-catalyzed alkenylation of δ-C(sp³)–H bonds with alkynes was conducted by density functional theory calculations. The present study shows that the dimeric Pd₂(OAc)₄ mechanism reproduces experimental observations well, including regioselectivity and provides a deep mechanistic insight complementing the monomeric Pd(OAc)₂ mechanism recently reported by Chen's group. In addition, the economical heterodimeric Ni–Pd(OAc)₄ was predicted to be a potential species for such alkenylation of δ-C(sp³)–H bonds.

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Supplementary files

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Article information

DOI: https://doi.org/10.1039/C8RA06077K
Article type: Paper
Submitted: 17 Jul 2018
Accepted: 20 Aug 2018
First published: 28 Aug 2018
This article is Open Access

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RSC Adv., 2018,8, 30186-30190

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Computational study on palladium-catalyzed alkenylation of remote δ-C(sp³)–H bonds with alkynes: a new understanding of mechanistic insight and origins of site-selectivity

H. Yan, Y. Tian, N. Li, R. Chang, Z. Zhang, X. Zhang, W. Yang, Z. Guo and Y. Li, RSC Adv., 2018, 8, 30186 DOI: 10.1039/C8RA06077K

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