DaPeng Zou

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Name: 邹大鹏; DaPeng Zou

Organization: Zhengzhou University

Department: 1 The College of Chemistry and Molecular Engineering

Title: Professor

TOPICS

Organic Chemistry

Hypervalent Iodine suzuki-miyaura Coupling

Chemicals
References

Palladium-Catalyzed Diastereoselective Synthesis of 3-Arylbutanoic Acid Derivatives

Co-reporter:Wubin Zhi, Jingya Li, Dapeng Zou, Yusheng Wu, and Yangjie Wu

The Journal of Organic Chemistry December 1, 2017 Volume 82(Issue 23) pp:12286-12286

Publication Date(Web):October 17, 2017

DOI:10.1021/acs.joc.7b02104

The first palladium-catalyzed diastereoselective conjugate addition of arylboronic acids to chiral imides is reported. The catalytic system employing 4-tert-butyloxazolidin-2-one as the chiral auxiliary in a mixed solvent system of MeOH/H2O (1:3) under an air atmosphere provides the optically active 3-arylbutanoic acid derivatives in excellent yields with high diastereoselectivity.

CuI-Catalyzed Fluorodesulfurization for the Synthesis of Monofluoromethyl Aryl Ethers

Co-reporter:Yang Geng, Apeng Liang, Xianying Gao, Chengshan Niu, Jingya Li, Dapeng Zou, Yusheng Wu, and Yangjie Wu

The Journal of Organic Chemistry August 18, 2017 Volume 82(Issue 16) pp:8604-8604

Publication Date(Web):July 13, 2017

DOI:10.1021/acs.joc.7b01438

An efficient CuI-catalyzed fluorodesulfurization for the synthesis of monofluoromethyl aryl ethers using DAST at room temperature has been developed. This approach exhibits a good functional group tolerance, a broad substrate scope, and a high synthesis efficiency.

Pd-catalyzed decarboxylative cross-coupling of sodium pyrimidinecarboxylates with (hetero)aryl bromides

Co-reporter:Shengqiang Wang, Hongtao Lu, Jingya Li, Dapeng Zou, Yusheng Wu, Yangjie Wu

Tetrahedron Letters 2017 Volume 58, Issue 28(Issue 28) pp:

Publication Date(Web):12 July 2017

DOI:10.1016/j.tetlet.2017.05.086

•An efficient method for the synthesis of 4- or 5-(hetero)arylpyrimidines has been developed.•The stable and easily available carboxylate salts were used as the nucleophilic coupling partner.•Pd-catalyzed decarboxylative cross-coupling was compatible with many functional groups.A straightforward method for the synthesis of functionalized 4- or 5-(hetero)arylpyrimidines via decarboxylative cross-coupling reaction from readily available pyrimidine-4- and pyrimidine-5-carboxylates was described. In the presence of dual-catalyst system of Pd(PPh3)4/Cu2O, the reaction proceeds smoothly, tolerates a variety of functional groups, and provides easy access to the synthesis of different (hetero)arylpyrimidines compounds.Download high-res image (57KB)Download full-size image

Copper-catalyzed remote CH ethoxycarbonyldifluoromethylation of 8-aminoquinolines with bis(pinacolato)diboron as reductant

Co-reporter:Shuaijun Han, Apeng Liang, Xiaoxiao Ren, Xianying Gao, Jingya Li, Dapeng Zou, Yangjie Wu, Yusheng Wu

Tetrahedron Letters 2017 Volume 58, Issue 52(Issue 52) pp:

Publication Date(Web):27 December 2017

DOI:10.1016/j.tetlet.2017.11.037

•A new approach to C5 ethoxycarbonyldifluoromethylation of quinolines.•Copper/B2pin2-catalyzed system was applied.•This catalytic system features mild conditions and good substrate tolerance.•The ethoxycarbonyldifluoromethylation of naphthalenes at C4 was firstly achieved.•The reaction proceeds under air.A simple protocol for the copper/B2pin2-catalyzed CH ethoxycarbonyldifluoromethylation of 8-aminoquinoline scaffolds with functionalized difluoromethyl bromides and iodines was developed, affording the desired products in moderate to good yields. This reaction was carried out under mild conditions and features good substrate tolerance.Download high-res image (92KB)Download full-size image

Synthesis of (E)-prop-1-ene-1,3-diyldibenzene derivatives via direct decarboxylative coupling of α,β-unsaturated carboxylic acids with benzyl boronic acid pinacol ester

Co-reporter:Mingxiang Zhu, Zhenjiang Qiu, Yun Zhang, Hongli Du, Jingya Li, Dapeng Zou, Yangjie Wu, Yusheng Wu

Tetrahedron Letters 2017 Volume 58, Issue 23(Issue 23) pp:

Publication Date(Web):7 June 2017

DOI:10.1016/j.tetlet.2017.04.084

•A facile and efficient strategy for the construction of (E)-prop-1-ene-1,3-diyldibenzene derivatives has been developed.•A broad range of (E)-prop-1-ene-1,3-diyldibenzene derivatives can be prepared from α,β-unsaturated carboxylic acids.•The decarboxylative cross-coupling is easy-handled and wide applicability.The first copper-catalyzed cross-coupling reaction between benzyl boronic acid pinacol ester and α,β-unsaturated carboxylic acids was described. The ready availability of the starting materials and excellent E selectivity make this protocol a safe and operationally convenient strategy for the efficient synthesis of (E)-prop-1-ene-1,3-diyldibenzene derivatives.Download high-res image (26KB)Download full-size image

Synthesis of (S)-3-hydroxytetrahydropyran from l-glutamic acid

Co-reporter:Yang Geng, Maolin Zheng, Jingya Li, Dapeng Zou, Yusheng Wu, Yangjie Wu

Tetrahedron Letters 2017 Volume 58, Issue 42(Issue 42) pp:

Publication Date(Web):18 October 2017

DOI:10.1016/j.tetlet.2017.09.008

•(S)-3-hydroxytetrahydropyran was synthesized from inexpensive l-glutamic acid.•One step intramolecular etherification was promoted by Tf2O under mild conditions.•The product was prepared with >95% ee in a gram-scale without recrystallization.A concise synthesis of (S)-3-hydroxytetrahydropyran from natural l-glutamic acid has been developed. The intramolecular etherification starting from 1,5-diol was promoted by trifluoromethanesulfonic anhydride. The clinnamates of the alcohols were prepared for accurately determining the optical purity by HPLC method.Download high-res image (54KB)Download full-size image

An efficient palladium-catalyzed synthesis of 1-heteroaryl-4-aminopiperidine derivatives from heteroaryl chlorides

Co-reporter:Kena Zhang, Hui Li, Jingya Li, Dapeng Zou, Yangjie Wu, Yusheng Wu

Tetrahedron Letters 2017 Volume 58, Issue 20(Issue 20) pp:

Publication Date(Web):17 May 2017

DOI:10.1016/j.tetlet.2017.04.014

•A facile and efficient strategy for the construction of 1-heteroaryl-4-aminopiperidine has been developed.•A broad range of 1-heteroaryl-4-(N-Boc-N-methyl)aminopiperidine can be prepared from relative heteroaryl chlorides.•The deprotection process is easy-handled and wide applicability.An efficient protocol for the synthesis of 1-heteroaryl-4-(N-methyl)aminopiperidines starting from heteroaryl chloride derivatives is described. A broad range of 1-heteroaryl-4-(N-Boc-N-methyl)aminopiperidine derivatives were obtained in good to excellent yields using DavePhos as optimal ligand for Pd-catalyzed Buchwald-Hartwig amination reaction. After a mild and efficient acidolysis the amination products could be obtained successfully.Download high-res image (44KB)Download full-size image

Metal-Free Reduction of Aromatic Nitro Compounds to Aromatic Amines with B2pin2 in Isopropanol

Co-reporter:Hongtao Lu, Zhiyue Geng, Jingya Li, Dapeng Zou, Yusheng Wu, and Yangjie Wu

Organic Letters 2016 Volume 18(Issue 11) pp:2774-2776

Publication Date(Web):May 23, 2016

DOI:10.1021/acs.orglett.6b01274

A metal-free reduction of aromatic nitro compounds to the corresponding amines has been achieved by a combination of B2pin2 and KOtBu in isopropanol. A series of nitro compounds containing various reducible functional groups were chemoselectively reduced in good to excellent yields.

Pd-catalyzed C–P coupling of heteroaryl boronic acid with H-phosphonate diester

Co-reporter:Zhiyue Geng, Yudan Zhang, Lu Zheng, Jingya Li, Dapeng Zou, Yangjie Wu, Yusheng Wu

Tetrahedron Letters 2016 Volume 57(Issue 29) pp:3063-3066

Publication Date(Web):20 July 2016

DOI:10.1016/j.tetlet.2016.05.038

•C–P bond was constructed under Pd–Ag catalyzed system without addition of base.•The method was done using commercial available heteroaryl boronic acid and H-phosphonate.•A new way to synthesize a variety of useful heteroaryl phosphonates.We report herein a novel protocol to construct C–P bond from heteroaryl boronic acid with H-phosphonate diester under Pd–Ag catalyzed system without addition of base. This method, directly using commercial available heteroaryl boronic acid as the starting material, provides a new way to synthesize a variety of useful heteroaryl phosphonates.

Regioselective Synthesis of N-Heteroaromatic Trifluoromethoxy Compounds by Direct OCF3 Bond Formation

Co-reporter:Apeng Liang;Shuaijun Han;Zhenwei Liu;Liang Wang;Dr. Jingya Li;Dr. Dapeng Zou;Dr. Yangjie Wu;Dr. Yusheng Wu

Chemistry - A European Journal 2016 Volume 22( Issue 15) pp:5102-5106

Publication Date(Web):

DOI:10.1002/chem.201505181

Abstract

The first one-step method for the synthesis of ortho-N-heteroaromatic trifluoromethoxy derivatives by site-specific O−CF₃ bond formation using hydroxylated N-heterocycles and Togni's reagent is described. The approach enables the unprecedented syntheses of a wide range of six or five-membered N-heteroaromatic trifluoromethoxy compounds containing one or two heteroatoms from most commonly used hydroxylated N-heterocycles. Notable advantages of this method include its simplicity and mild conditions, avoidance of the need for metals or toxic reagents, and compatibility with a variety of functional groups. Furthermore, this method is especially suitable for the larger scale application.

Facile synthesis of trifluoroethyl aryl ethers through copper-catalyzed coupling of CF3CH2OH with aryl- and heteroaryl boronic acids

Co-reporter:Ruixin Wang, Liang Wang, Kena Zhang, Jingya Li, Dapeng Zou, Yangjie Wu, Yusheng Wu

Tetrahedron Letters 2015 Volume 56(Issue 33) pp:4815-4818

Publication Date(Web):12 August 2015

DOI:10.1016/j.tetlet.2015.06.066

An efficient copper-catalyzed Chan–Lam reaction of trifluoroethanol with a variety of aryl- and heteroaryl boronic acids has been developed. This research provides a practical method to synthesize trifluoroethyl aryl ethers in moderate to good yields under mild conditions.

Efficient synthesis of diarylmethane derivatives by PdCl2 catalyzed cross-coupling reactions of benzyl chlorides with aryl boronic acids in aqueous medium

Co-reporter:Guangkuan Zhao, Kena Zhang, Liang Wang, Jingya Li, Dapeng Zou, Yangjie Wu, Yusheng Wu

Tetrahedron Letters 2015 Volume 56(Issue 48) pp:6700-6703

Publication Date(Web):2 December 2015

DOI:10.1016/j.tetlet.2015.10.053

The research provides a simple and efficient method for preparing diarylmethane derivatives using the cross-coupling reaction of benzyl chlorides and aryl boronic acids catalyzed by palladium chloride in DMF aqueous solution without additional ligand.

One-Pot Double Benzylation of 2-Substituted Pyridines using Palladium-Catalyzed Decarboxylative Coupling of sp2 and sp3 Carbons

Co-reporter:Yaping Wang;Xinjian Li;Faqiang Leng;Helong Zhu;Jingya Li;Yangjie Wu;Yusheng Wu

Advanced Synthesis & Catalysis 2014 Volume 356( Issue 16) pp:3307-3313

Publication Date(Web):

DOI:10.1002/adsc.201400311

A Metal-Free Route to CF3-Containing Oxindoles by PhI(OAc)2-Mediated Trifluoromethylation of N-Arylacrylamides with TMSCF3

Co-reporter:Weijun Fu;Fengjuan Xu;Yuqin Fu;Chen Xu;Shihui Li

European Journal of Organic Chemistry 2014 Volume 2014( Issue 4) pp:709-712

Publication Date(Web):

DOI:10.1002/ejoc.201301512

Abstract

A mild and efficient PhI(OAc)₂-mediated trifluoromethylation reaction of N-arylacrylamides with TMSCF₃ under metal-free conditions was developed. This method provides convenient access to a variety of useful CF₃-containing oxindoles in moderate to good yields.

Cucurbit[7]uril promoting PdCl2-catalyzed cross-coupling reaction of benzyl halides and arylboronic acids in aqueous media

Co-reporter:Guangkuan Zhao, Zhen Wang, Ruixin Wang, Jingya Li, Dapeng Zou, Yangjie Wu

Tetrahedron Letters 2014 Volume 55(Issue 38) pp:5319-5322

Publication Date(Web):17 September 2014

DOI:10.1016/j.tetlet.2014.07.060

The research provides a novel approach for producing diarylmethane derivatives using CB[7]–NaCl–PdCl2 catalyzed Suzuki cross-coupling reaction of benzyl chloride derivatives and arylboronic acids in ethanol aqueous solution.

Facile synthesis of trifluoroethyl compounds by the Suzuki cross-coupling reactions of CF3CH2OTs with arylboronic acids

Co-reporter:Faqiang Leng, Yaping Wang, Hui Li, Jingya Li, Dapeng Zou, Yangjie Wu and Yusheng Wu

Chemical Communications 2013 vol. 49(Issue 91) pp:10697-10699

Publication Date(Web):27 Sep 2013

DOI:10.1039/C3CC46601A

This research provides a novel approach for introducing a CF3CH2 group onto aromatic rings using Pd(OAc)2/palladacycle as a catalyst for the Suzuki cross-coupling reaction of CF3CH2OTs (OTs = 4-methylbenzene sulfonate) with arylboronic acids.

Formation and Rupture of a Supramolecular Nanocapsule Triggered onoffon Supramolecular Switch for Zn2+

Co-reporter:Song Jiang;Man Liu;Yanting Cui, ;Yangjie Wu

European Journal of Organic Chemistry 2013 Volume 2013( Issue 13) pp:

Publication Date(Web):

DOI:10.1002/ejoc.201201416

Abstract

A novel selective fluorescence probe that contains 2-p-phenylimidazo[4,5-f][1,10]phenanthroline and a viologen unit linked by a flexible chain was synthesized and found to be able to select zinc ions with a clear fluorescence enhancement and a large stokes shift in aqueous solution. This probe can also be designed as an on–off–on molecular switch by the formation and rupture of a supramolecular nanocapsule with cucurbit[8]uril (CB[8]) in aqueous solution.

Guest-size determining the selective binding modes of cucurbit[8]uril, electron-rich guests and N-alkyl-N′-methyl-4,4′-bipyridinium

Co-reporter:Song jiang, Xiaona Yang, Chunxue Yang, Mingqiong Tong, Dapeng Zou, Yangjie Wu

Tetrahedron Letters 2013 Volume 54(Issue 13) pp:1638-1644

Publication Date(Web):27 March 2013

DOI:10.1016/j.tetlet.2012.12.120

The supramolecular self-assembly in aqueous solution of N-alkyl-N′-methyl-4,4′-bipyridinium ([CmMV]2+) (m = 4, 5, 7, 12), 1,4-dihydroxybenzene (HB), and 2,6-dihydroxynaphthalene (HN) with cucurbit[8]uril (CB[8]) was investigated with 1H NMR, NOESY, ESI-MS, and UV–vis spectroscopy. It has been reported that these three compounds ([CmMV]2+ (m = 12), HN and CB[8]) can form 1:1:1 inclusion complex with the C12 alkyl chain of [C12MV]2+ being present outside the cavity. Here we report that [CmMV]2+ (m ⩾5), HB, and CB[8] can form a new supramolecular self-assembly binding mode with the alkyl chain being present inside the cavity.

Highly efficient synthesis of aryl and heteroaryl trifluoromethyl ketones via o-iodobenzoic acid (IBX)

Co-reporter:Huicheng Cheng, Yu Pei, Faqiang Leng, Jingya Li, Apeng Liang, Dapeng Zou, Yangjie Wu, Yusheng Wu

Tetrahedron Letters 2013 Volume 54(Issue 33) pp:4483-4486

Publication Date(Web):14 August 2013

DOI:10.1016/j.tetlet.2013.06.045

A two-step process for the synthesis of aryl and heteroaryl trifluoromethyl ketones from the corresponding aldehydes is described. Trifluoromethyl alcohols were prepared from aryl and heteroaryl aldehydes in excellent yields using catalytic amount of K2CO3. The trifluoromethyl alcohols were then oxidized conveniently and efficiently by o-iodoxybenzoic acid (IBX) under mild conditions to get the desired functionalized aryl and heteroaryl trifluoromethyl ketones.

Synthesis of functionalized 3-arylpyridazines via Pd-catalyzed decarboxylative cross-coupling of pyridazine-3-carboxylic acids

Co-reporter:Shengqiang Wang, Hongtao Lu, Jingya Li, Dapeng Zou, Yusheng Wu, Yangjie Wu

Tetrahedron Letters (22 March 2017) Volume 58(Issue 12) pp:1107-1111

Publication Date(Web):22 March 2017

DOI:10.1016/j.tetlet.2017.01.083

Copper-catalyzed decarboxylative trifluoroethylation of cinnamic acids

Co-reporter:Yun Zhang, Hongli Du, Mingxiang Zhu, Jingya Li, Dapeng Zou, Yangjie Wu, Yusheng Wu

Tetrahedron Letters (1 March 2017) Volume 58(Issue 9) pp:880-883

Publication Date(Web):1 March 2017

DOI:10.1016/j.tetlet.2017.01.060

Efficient synthesis of pyrazine boronic esters via palladium-catalyzed Miyaura borylation

Co-reporter:Hongtao Lu, Shengqiang Wang, Jingya Li, Dapeng Zou, Yusheng Wu, Yangjie Wu