Ruthenium-Catalyzed 1,6-Hydroalkylation of para-Quinone Methides with Ketones via the in Situ Activation of C(sp3)-H Bonds

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期刊论文

作者：

Shang, Wenli;Zhu, Longzhi;Li, Zikang;Xu, Weifeng;Xiong, Biquan*;...

通讯作者：

Xiong, BQ;Xiong, Biquan;Wong, WY;Yin, SF

作者机构：

[Liu, Yu; Tang, Ke-Wen; Xu, Weifeng; Shang, Wenli; Xiong, Biquan; Zhu, Longzhi] Hunan Inst Sci & Technol, Dept Chem & Chem Engn, Yueyang 414006, Peoples R China.

[Li, Zikang; Wong, Wai-Yeung; Xiong, Biquan] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hung Hom, Hong Kong 999077, Peoples R China.

[Li, Zikang; Wong, Wai-Yeung; Xiong, Biquan] Hong Kong Polytech Univ, Res Inst Smart Energy, Hung Hom, Hong Kong 999077, Peoples R China.

[Qian, Peng-Cheng] Wenzhou Univ, Inst New Mat & Ind Technol, Coll Chem & Mat Engn, Key Lab Environm Funct Mat Technol & Applicat Wenz, Wenzhou 325035, Peoples R China.

[Yin, Shuang-Feng; Yin, SF] Hunan Univ, Coll Chem & Chem Engn, Adv Catalyt Engn Res Ctr, Minist Educ,State Key Lab Chemo Biosensing & Chemo, Changsha 410082, Peoples R China.

通讯机构：

[Xiong, BQ; Xiong, BQ ; Wong, WY ; Yin, SF ] H

Hunan Inst Sci & Technol, Dept Chem & Chem Engn, Yueyang 414006, Peoples R China.

Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hung Hom, Hong Kong 999077, Peoples R China.

Hong Kong Polytech Univ, Res Inst Smart Energy, Hung Hom, Hong Kong 999077, Peoples R China.

Hunan Univ, Coll Chem & Chem Engn, Adv Catalyt Engn Res Ctr, Minist Educ,State Key Lab Chemo Biosensing & Chemo, Changsha 410082, Peoples R China.

语种：

英文

关键词：

Catalysis;Chemical activation;Quinone;Ruthenium;Control experiments;DFT calculation;Gain insight;H-bonds;Hydroalkylation;Quinone methide;Reaction mechanism;Simple++;Situ activation;Step control;Ketones;ketone derivative;oxidizing agent;polycyclic aromatic hydrocarbon derivative;quinone derivative;ruthenium;alkylation;Article;catalysis;controlled study;density functional theory;hydrogen bond;methylation;organic synthesis;quantum yield;reaction analysis;reaction optimization;regioselectivity

期刊：

JOURNAL OF ORGANIC CHEMISTRY

ISSN：

0022-3263

年：

2023

卷：

期：

页码：

16196-16215

DOI：

10.1021/acs.joc.3c01661

基金类别：

This work was supported by the National Natural Science Foundation of China (21725602, 21908050), Natural Science Foundation of Hunan Province (2023JJ30274, 2023JJ30275) and the Opening Project of Wenzhou Association for Science and Technology (WZAST). W.-Y.W. thanks the CAS-Croucher Funding Scheme for Joint Laboratories, ITC Guangdong-Hong Kong Technology Cooperation Funding Scheme (TCFS) (GHP/038/19GD), Research Institute for Smart Energy (CDAQ) and the Endowed Professorship in Energy from Miss Clarea Au (847S) for financial support.

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本校为通讯机构

院系归属：

理学院

摘要：

A simple and efficient method for the ruthenium-catalyzed 1,6-hydroalkylation of para-quinone methides (p-QMs) with ketones via the in situ activation of C(sp3)-H bonds has been disclosed. Without the need for preactivation of the substrates and oxidant, a broad range of p-QMs and ketones are well tolerated, producing the expected 1,6-hydroalkylation products with moderate to good yields. Step-by-step control experiments and DFT calculation were conducted systematically to gain insights for the plausible reaction mechanism. This finding may hav...

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Ruthenium-Catalyzed 1,6-Hydroalkylation of para-Quinone Methides with Ketones via the in Situ Activation of C(sp3)-H Bonds

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