Renhua Liu

Name: 刘仁华; Liu, RenHua

Organization: East China University of Science and Technology , China

Department: School of Pharmacy

Title: Professor(PhD)

Chemicals
References

C–H Functionalization via Remote Hydride Elimination: Palladium Catalyzed Dehydrogenation of ortho-Acyl Phenols to Flavonoids

Co-reporter:Xiaomei Zhao, Jiabin Zhou, Shuying Lin, Xukang Jin, and Renhua Liu

Organic Letters 2017 Volume 19(Issue 5) pp:

Publication Date(Web):February 13, 2017

DOI:10.1021/acs.orglett.6b03652

Although deprotonation of electron-poor C–H bonds to carbon anions with bases has long been known and widely used in organic synthesis, the hydride elimination from electron-rich C–H bonds to carbon cations or partial carbocations for the introduction of nucleophiles is a comparatively less explored area. Here we report that the carbonyl β-C(sp3)–H bond hydrogens of ortho-acyl phenols could be substituted by intramolecular phenolic hydroxyls to form O-heterocycles, followed by dehydrogenation of the O-heterocycle into flavonoids. The cascade reaction is catalyzed by Pd/C without added oxidants and sacrificing hydrogen acceptors.

One-Step Synthesis of Substituted Benzofurans from ortho- Alkenylphenols via Palladium-Catalyzed CH Functionalization

Co-reporter:Dejun Yang;Yifei Zhu;Na Yang;Qiangqiang Jiang

Advanced Synthesis & Catalysis 2016 Volume 358( Issue 11) pp:1731-1735

Publication Date(Web):

DOI:10.1002/adsc.201600082

Reaction-activated palladium catalyst for dehydrogenation of substituted cyclohexanones to phenols and H2 without oxidants and hydrogen acceptors

Co-reporter:Jingwu Zhang, Qiangqiang Jiang, Dejun Yang, Xiaomei Zhao, Yanli Dong and Renhua Liu

Chemical Science 2015 vol. 6(Issue 8) pp:4674-4680

Publication Date(Web):19 May 2015

DOI:10.1039/C5SC01044F

It is widely believed that the dehydrogenation of organic compounds is a thermodynamically unfavorable process, and thus requires stoichiometric oxidants such as dioxygen and metal oxides or sacrificial hydrogen acceptors to remove the hydrogen from the reaction mixture to drive the equilibrium towards the products. Here we report a previously unappreciated combination of common commercial Pd/C and H2 which dehydrogenates a wide range of substituted cyclohexanones and 2-cyclohexenones to their corresponding phenols with high isolated yields, with H2 as the only byproduct. The reaction requires no oxidants or hydrogen acceptors because instead of removing the generated hydrogen with oxidants or hydrogen acceptors, we demonstrated it can be used as a cocatalyst to help power the reaction. This method for phenol synthesis manifests a high atom economy, and is inherently devoid of the complications normally associated with oxidative dehydrogenations.

4-OH-TEMPO/TCQ/TBN/HCl: A Metal-Free Catalytic System for Aerobic Oxidation of Alcohols under Mild Conditions

Co-reporter:Yanli Dong;Xiaomei Zhao

Chinese Journal of Chemistry 2015 Volume 33( Issue 9) pp:1019-1023

Publication Date(Web):

DOI:10.1002/cjoc.201500357

Abstract

A green and economical catalyst system, 4-OH-TEMPO/TCQ/TBN/HCl, for the aerobic oxidation of a broad range of primary and secondary alcohols to the corresponding carbonyl compounds has been developed. These reactions proceed without transition-metals under mild conditions with excellent yields.

Ruthenium Trichloride Catalyzed Highly Efficient Deoximation of Oximes to the Carbonyl Compounds and Nitriles without Acceptors

Co-reporter:Yuxiao Liu;Na Yang;Changhu Chu

Chinese Journal of Chemistry 2015 Volume 33( Issue 9) pp:1011-1014

Publication Date(Web):

DOI:10.1002/cjoc.201500325

Abstract

An acceptor-free catalysis protocol for the deoximation of ketoximes and aldoximes using RuCl₃ as the catalyst has been developed. Under the optimized conditions, various oximes were converted to ketones and nitriles with excellent isolated yields.

Copper-Catalyzed Aerobic Oxidative Coupling of Aromatic Alcohols and Acetonitrile to β-Ketonitriles

Co-reporter:Jiaxuan Shen, Dejun Yang, Yuxiao Liu, Shuangshuang Qin, Jingwu Zhang, Jiangkai Sun, Chunhui Liu, Chaoyang Liu, Xiaomei Zhao, Changhu Chu, and Renhua Liu

Organic Letters 2014 Volume 16(Issue 2) pp:350-353

Publication Date(Web):January 6, 2014

DOI:10.1021/ol403555n

A practical, convenient, and cheap copper-catalyzed aerobic oxidative coupling of aromatic alcohols and acetonitrile to β-ketonitriles has been developed. The green C–C bond formation involving the loss of two hydrogen atoms from the corresponding two carbons, respectively, unlocks opportunities for markedly different synthetic strategies.

4-Benzamido-TEMPO Catalyzed Oxidation of a Broad Range of Alcohols to the Carbonyl Compounds with NaBrO3 under Mild Conditions

Co-reporter:Jiaxuan Shen;Jiangkai Sun;Shuangshuang Qin;Changhu Chu

Chinese Journal of Chemistry 2014 Volume 32( Issue 5) pp:405-409

Publication Date(Web):

DOI:10.1002/cjoc.201400141

Abstract

4-Benzamido-TEMPO catalyzed oxidation system for conversion of a wide range of alcohols to the aldehydes or ketones with NaBrO₃ under room temperature conditions has been developed. The credible, operationally convenient and economical, and condition mild oxidation protocol is particularly of interest in laboratory and in fine chemicals manufacture.

Formation of CN bonds by the release of H2: a new strategy for synthesis of imines and benzazoles

Co-reporter:Xukang Jin, Yuxiao Liu, Qiongqiong Lu, Dejun Yang, Jiangkai Sun, Shuangshuang Qin, Jingwu Zhang, Jiaxuan Shen, Changhu Chu and Renhua Liu

Organic & Biomolecular Chemistry 2013 vol. 11(Issue 23) pp:3776-3780

Publication Date(Web):22 Apr 2013

DOI:10.1039/C3OB40388B

A new strategy for synthesis of imines using the approach of release of H2 has been developed. This oxidant- and acceptor-free Pd/C catalysis protocol is further applied to synthesis of benzoxazoles, benzimidazoles, and benzothiazoles through a one-pot cascade reaction with notably high yields.

Iron Chloride/4-Acetamido-TEMPO/Sodium Nitrite-Catalyzed Aerobic Oxidation of Primary Alcohols to the Aldehydes

Co-reporter:Weili Yin;Changhu Chu;Qiongqiong Lu;Jianwei Tao;Xinmiao Liang

Advanced Synthesis & Catalysis 2010 Volume 352( Issue 1) pp:113-118

Publication Date(Web):

DOI:10.1002/adsc.200900662

Abstract

A variety of 4-substituted 2,2,6,6-tetramethylpiperidyl-1-oxy (TEMPO) derivatives has been screened for their ability in the oxidation of primary alcohols to the aldehydes with dioxygen under mild conditions. An evaluation of the efficiency of these 4-substituted TEMPO derivatives in the alcohol oxidation may allow an insight into the effect of the structural variations of TEMPO on the oxidation of alcohols, which should facilitate catalyst design and screening efforts. Based on the screening results of 4-substituted TEMPO derivatives, the catalyst comprised of 4-acetamido-TEMPO, iron chloride and sodium nitrite, has been developed for the highly efficient oxidation of a wide range of primary alcohols including primary aliphatic alcohols to the corresponding aldehydes under mild conditions.

NaNO2/FeCl3 dioxygen recyclable activator: An efficient approach to active oxygen species for degradation of a broad range of organic dye pollutants in water

Co-reporter:Yanrong Peng, Dongmei Fu, Renhua Liu, Feifang Zhang, Xingya Xue, Qing Xu, Xinmiao Liang

Applied Catalysis B: Environmental (28 February 2008) Volume 79(Issue 2) pp:163-170

Publication Date(Web):28 February 2008

DOI:10.1016/j.apcatb.2007.10.017

Reaction-activated palladium catalyst for dehydrogenation of substituted cyclohexanones to phenols and H2 without oxidants and hydrogen acceptors

Co-reporter:Jingwu Zhang, Qiangqiang Jiang, Dejun Yang, Xiaomei Zhao, Yanli Dong and Renhua Liu

Chemical Science (2010-Present) 2015 - vol. 6(Issue 8) pp:NaN4680-4680

Publication Date(Web):2015/05/19

DOI:10.1039/C5SC01044F

Formation of CN bonds by the release of H2: a new strategy for synthesis of imines and benzazoles

Co-reporter:Xukang Jin, Yuxiao Liu, Qiongqiong Lu, Dejun Yang, Jiangkai Sun, Shuangshuang Qin, Jingwu Zhang, Jiaxuan Shen, Changhu Chu and Renhua Liu