Yong-ming Zhu

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Organization: Soochow University

Department: College of Pharmaceutical Sciences

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TOPICS

Organic Chemistry

Formylation Cyanation

Chemicals
References

Palladium-catalyzed carbonylative synthesis of isocoumarins and phthalides by using phenyl formate as a carbon monoxide source

Co-reporter:Qing Yuan;Zhen-Bang Chen;Fang-Ling Zhang

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 7) pp:1628-1635

Publication Date(Web):2017/02/15

DOI:10.1039/C6OB02409B

A simple and efficient palladium-catalyzed intramolecular carbonylative synthesis of isocoumarins and phthalides from the easily available starting materials by employing phenyl formate as a CO surrogate has been achieved. The approach affords target compounds in good to excellent yields with the advantages of lower toxicity, milder conditions, easy operation and wide functional group tolerance.

Palladium-catalyzed oxidative coupling of arylboronic acid with isocyanide to form aromatic carboxylic acids

Co-reporter:Zhen-Bang Chen;Kui Liu;Fang-Ling Zhang;Qing Yuan

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 38) pp:8078-8083

Publication Date(Web):2017/10/04

DOI:10.1039/C7OB01428G

A valuable palladium-catalyzed oxidative coupling of aryl- and alkenyl borides with isocyanide for the synthesis of corresponding carboxylic acids has been developed. With wide substrate scopes and good functional group tolerance, this reaction offers corresponding carboxylic acids in moderate to excellent yields.

Palladium-Catalyzed Synthesis of α-Iminonitriles from Aryl Halides via Isocyanide Double Insertion Reaction

Co-reporter:Zhen-Bang Chen, Ying Zhang, Qing Yuan, Fang-Ling Zhang, Yong-Ming Zhu, and Jing-Kang Shen

The Journal of Organic Chemistry 2016 Volume 81(Issue 4) pp:1610-1616

Publication Date(Web):January 27, 2016

DOI:10.1021/acs.joc.5b02777

An efficient one-pot synthesis of α-iminonitriles from readily available aryl halides via palladium-catalyzed double isocyanide insertion and elimination has been developed, without using various hypertoxic cyanides and excess oxidants. Furthermore, the utility of this reaction was demonstrated by the rapid total synthesis of quinoxaline and the reaction of functional groups exchanged with aryl halides.

Palladium-catalyzed chemoselective synthesis of indane-1,3-dione derivatives via tert-butyl isocyanide insertion

Co-reporter:Huaqing Duan, Zhong Chen, Li Han, Yulin Feng, Yongming Zhu and Shilin Yang

Organic & Biomolecular Chemistry 2015 vol. 13(Issue 24) pp:6782-6788

Publication Date(Web):11 May 2015

DOI:10.1039/C5OB00472A

A simple and efficient strategy for the synthesis of indane-1,3-dione derivatives through a palladium(0)-catalyzed reaction incorporating tert-butyl isocyanide has been developed. In addition, by applying this protocol as the key step, indenopyrazole derivatives can be easily synthesized in high yields in a one-pot procedure. This methodology is tolerant of a wide range of substrates and applicable to library synthesis.

Palladium-catalyzed one-pot synthesis of diazoles via tert-butyl isocyanide insertion

Co-reporter:Xiang-Yuan Fan, Xiao Jiang, Ying Zhang, Zhen-Bang Chen and Yong-Ming Zhu

Organic & Biomolecular Chemistry 2015 vol. 13(Issue 41) pp:10402-10408

Publication Date(Web):19 Aug 2015

DOI:10.1039/C5OB01328C

An efficient one-pot palladium-catalyzed reaction for the synthesis of diazoles from readily available hydrazides and aryl halide via isocyanide insertion/cyclization sequence has been developed. This methodology efficiently constructs diazoles in good to excellent yields with the advantages of wide functional group tolerance and operational simplicity.

Palladium-catalyzed synthesis of aldehydes from aryl halides and tert-butyl isocyanide using formate salts as hydride donors

Co-reporter:Ying Zhang, Xiao Jiang, Jin-Mei Wang, Jing-Lei Chen and Yong-Ming Zhu

RSC Advances 2015 vol. 5(Issue 22) pp:17060-17063

Publication Date(Web):29 Jan 2015

DOI:10.1039/C4RA16388E

An efficient one-pot palladium-catalyzed hydroformylation of aryl halides to produce aromatic aldehydes has been achieved, employing tert-butyl isocyanide as a C1 resource and formate salt as a hydride donor without any additional bases. Characterized by its mild reaction conditions, easy operation and lower toxicity, this reaction can tolerate a wide array of functional groups with moderate to excellent yields.

Synthesis, cytotoxicity and haemolytic activity of Pulsatilla saponin A, D derivatives

Co-reporter:Zhong Chen, Huaqing Duan, Minglei Wang, Li Han, Yanli Liu, Yongming Zhu, Shilin Yang

Bioorganic & Medicinal Chemistry Letters 2015 Volume 25(Issue 12) pp:2550-2554

Publication Date(Web):15 June 2015

DOI:10.1016/j.bmcl.2015.04.049

The strong haemolytic activity of Pulsatilla saponin A (PSA), D (PSD) hampered their clinical development of antitumor agents. In order to solve this problem, C-28 position modification derivatives of PSA/PSD were synthesized. The cytotoxicity and haemolytic activity of these compounds were evaluated. Structure–activity relationship and structure–toxicity relationship had been observed. The mice acute toxicity of compound 11 was reduced greatly than that of PSA. This study indicates that compound 11 may represent an interesting class of potent antitumor agents from triterpenoid saponins avoiding the haemolysis problem. The present study has important significance for the development of antitumor saponins.

Palladium-catalyzed synthesis of 4H-benzo[d][1,3]oxazin-4-ones and N-(2-cyanophenyl)benzamides via tert-butyl isocyanide insertion

Co-reporter:Jin-Mei Wang, Xiao Jiang, Ying Zhang, Yong-Ming Zhu, Jing-Kang Shen

Tetrahedron Letters 2015 Volume 56(Issue 18) pp:2349-2354

Publication Date(Web):29 April 2015

DOI:10.1016/j.tetlet.2015.03.121

A novel and efficient palladium-catalyzed strategy via tert-butyl isocyanide insertion from N-(2-bromophenyl)benzamides has been developed. Treatment of the same imine intermediates with FeCl3 gives 4H-benzo[d][1,3]oxazin-4-ones, whereas with AlCl3 delivers N-(2-cyanophenyl)benzamides.

Palladium-Catalyzed Carbonylative Annulation Reactions Using Aryl Formate as a CO Source: Synthesis of 2-Substituted Indene-1,3(2H)-dione Derivatives

Co-reporter:Ying Zhang, Jing-Lei Chen, Zhen-Bang Chen, Yong-Ming Zhu, and Shun-Jun Ji

The Journal of Organic Chemistry 2015 Volume 80(Issue 21) pp:10643-10650

Publication Date(Web):October 9, 2015

DOI:10.1021/acs.joc.5b01758

An efficient synthesis of 2-substituted indene-1,3(2H)-diones from stable and readily available 1-(2-halophenyl)-1,3-diones by employing phenyl formate as a CO source has been developed. The reaction occurred via palladium-catalyzed intramolecular carbonylative annulation using K3PO4 as a base and DMSO as a solvent at 95 °C. In this protocol, the reaction showed a broad substrate scope with good to excellent yields.

Synthesis of aryl nitriles by palladium-assisted cyanation of aryl iodides using tert-butyl isocyanide as cyano source

Co-reporter:Xiao Jiang, Jin-Mei Wang, Ying Zhang, Zhong Chen, Yong-Ming Zhu, Shun-Jun Ji

Tetrahedron 2015 Volume 71(Issue 29) pp:4883-4887

Publication Date(Web):22 July 2015

DOI:10.1016/j.tet.2015.04.059

A palladium-catalyzed synthesis of aryl nitriles by the cyanation of aryl iodides with tert-butyl isocyanide as cyano source has been developed. This novel and efficient method avoids the use of toxic cyanides. The reaction is easy-to-handle and shows good functional group compatibility.

Palladium-Catalyzed Domino Synthesis of 4-Amino-3-acyl-2- naphthols via Isocyanide Chemoselective Insertion

Co-reporter:Zhong Chen, Hua-Qing Duan, Xiao Jiang, Yong-Ming Zhu, Shun-Jun Ji, and Shi-Lin Yang

The Journal of Organic Chemistry 2015 Volume 80(Issue 16) pp:8183-8188

Publication Date(Web):August 6, 2015

DOI:10.1021/acs.joc.5b01269

A novel and efficient strategy for the synthesis of sterically hindered 4-amino-3-acyl-2-naphthols through a palladium-catalyzed coupling reaction involving isocyanide chemselective insertion and domino isomerization has been developed. The methodology, which is in accordance with the principle of “atom and step economy”, efficiently constructs 4-amino-3-acyl-2-naphthols in moderate to good yields.

Palladium-Catalyzed Formylation of Aryl Halides with tert-Butyl Isocyanide

Co-reporter:Xiao Jiang, Jin-Mei Wang, Ying Zhang, Zhong Chen, Yong-Ming Zhu, and Shun-Jun Ji

Organic Letters 2014 Volume 16(Issue 13) pp:3492-3495

Publication Date(Web):June 23, 2014

DOI:10.1021/ol5014262

A novel palladium-catalyzed formylation of aryl halides with isocyanide in the presence of Et3SiH has been demonstrated, which provides a strategy toward important aldehydes with moderate to excellent yield. The advantage of this reaction includes milder conditions, convenient operation, lower toxicity, and wide functional group tolerance.

Divergent synthesis of 6H-isoindolo[2,1-a]indol-6-ones and indenoindolones: an investigation of Pd-catalyzed isocyanide insertion

Co-reporter:Ting Tang, Xiao Jiang, Jin-Mei Wang, Yin-Xing Sun, Yong-Ming Zhu

Tetrahedron 2014 70(18) pp: 2999-3004

Publication Date(Web):

DOI:10.1016/j.tet.2014.03.018

Palladium-Catalyzed One-Pot Synthesis of Quinazolinones via tert-Butyl Isocyanide Insertion

Co-reporter:Xiao Jiang, Ting Tang, Jin-Mei Wang, Zhong Chen, Yong-Ming Zhu, and Shun-Jun Ji

The Journal of Organic Chemistry 2014 Volume 79(Issue 11) pp:5082-5087

Publication Date(Web):May 8, 2014

DOI:10.1021/jo500636y

A novel palladium-catalyzed three-component reaction for the synthesis of quinazolin-4(3H)-ones from readily available 2-aminobenzamides and aryl halides via a palladium-catalyzed isocyanide insertion/cyclization sequence has been developed. This methodology efficiently constructs quinazolin-4(3H)-ones in moderate to excellent yields with the advantages of operational simplicity.

Copper-Catalyzed C–N Bond Formation/Rearrangement Sequence: Synthesis of 4H-3,1-Benzoxazin-4-ones

Co-reporter:Zhi-Yuan Ge, Qiong-Ming Xu, Xiang-Dong Fei, Ting Tang, Yong-Ming Zhu, and Shun-Jun Ji

The Journal of Organic Chemistry 2013 Volume 78(Issue 9) pp:4524-4529

Publication Date(Web):April 12, 2013

DOI:10.1021/jo400515y

A facile and efficient copper-catalyzed method for the synthesis of 4H-3,1-benzoxazin-4-one derivatives has been developed. This procedure is based on a tandem intramolecular C–N coupling/rearrangement process. This method would provide a new and useful strategy for construction of N-heterocycles.

Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides via tert-Butyl Isocyanide Insertion

Co-reporter:Ting Tang, Xiang-Dong Fei, Zhi-Yuan Ge, Zhong Chen, Yong-Ming Zhu, and Shun-Jun Ji

The Journal of Organic Chemistry 2013 Volume 78(Issue 7) pp:3170-3175

Publication Date(Web):February 25, 2013

DOI:10.1021/jo4001096

A simple and efficient palladium-catalyzed carbonylative Sonogashira coupling via tert-butyl isocyanide insertion has been developed, which demonstrates the utility of isocyanides in intermolecular C–C bond construction. This methodology provides a novel pathway for the synthesis of alkynyl imines which can undergo simple silica gel catalyzed hydrolysis to afford alkynones. The approach is tolerant of a wide range of substrates and applicable to library synthesis.

BuchwaldHartwig Coupling/Michael Addition Reactions: One-Pot Synthesis of 1,2-Disubstituted 4-Quinolones from Chalcones and Primary Amines

Co-reporter:Xiang-Dong Fei;Zhou Zhou;Wen Li;Jing-Kang Shen

European Journal of Organic Chemistry 2012 Volume 2012( Issue 15) pp:3001-3008

Publication Date(Web):

DOI:10.1002/ejoc.201200172

Abstract

The Buchwald–Hartwig coupling/Michael addition sequence has been successfully applied to the synthesis of functionalized 1,2-disubstituted 4-quinolones using Pd(OAc)₂ as a catalyst and PPh₃ as a ligand. Under these conditions, the intermediate products first formed from chalcones and primary amines underwent catalytic dehydrogenation to yield the 1,2-disubstituted 4-quinolones.

Palladium-Catalyzed Synthesis of Isocoumarins and Phthalides via tert-Butyl Isocyanide Insertion

Co-reporter:Xiang-Dong Fei, Zhi-Yuan Ge, Ting Tang, Yong-Ming Zhu, and Shun-Jun Ji

The Journal of Organic Chemistry 2012 Volume 77(Issue 22) pp:10321-10328

Publication Date(Web):October 26, 2012

DOI:10.1021/jo302004u

A novel and highly efficient strategy for the synthesis of isocoumarins and phthalides through a palladium(0)-catalyzed reaction incorporating tert-butyl isocyanide has been developed. This process, providing one of the simplest methods for the synthesis of this class of valuable lactones, involves two steps including cyclization reaction and simple acid hydrolysis. The methodology is tolerant of a wide range of substrates and applicable to library synthesis.

Synthesis of 3-Substituted Isocoumarins via a Cascade Intramolecular Ullmann-Type Coupling–Rearrangement Process

Co-reporter:Zhi-Yuan Ge, Xiang-Dong Fei, Ting Tang, Yong-Ming Zhu, and Jing-Kang Shen

The Journal of Organic Chemistry 2012 Volume 77(Issue 13) pp:5736-5743

Publication Date(Web):June 7, 2012

DOI:10.1021/jo300916s

A simple and highly efficient strategy for the synthesis of 3-substituted isocoumarins through a copper(I)-catalyzed reaction of 1-(2-halophenyl)-1,3-diones has been developed. The procedure is based on a cascade copper-catalyzed intramolecular Ullmann-type C-arylation and rearrangement process. This methodology is tolerant of a wide range of substrates and applicable to library synthesis.

Metal-Free Intramolecular Amination: One-Pot Tandem Synthesis of 3-Substituted 4-Quinolones

Co-reporter:Qi-Lun Liu, Qiu-Lian Li, Xiang-Dong Fei, and Yong-Ming Zhu

ACS Combinatorial Science 2011 Volume 13(Issue 1) pp:19

Publication Date(Web):November 9, 2010

DOI:10.1021/co1000103

3-Substituted 4-quinolones were synthesized using a one-pot metal-free strategy in moderate to quantitative yields. Carried out in dimethylsulfoxide (DMSO) via a sequential addition of materials, the methodology is tolerant of a wide range of functional groups and applicable to library synthesis.Keywords (keywords): intramolecular amination; metal-free; one-pot; quinolones

A Novel Synthesis of Isoflavones via Copper(I)-Catalyzed Intramolecular Cyclization Reaction

Co-reporter:Qiu-Lian Li;Qi-Lun Liu;Zhi-Yuan Ge

Helvetica Chimica Acta 2011 Volume 94( Issue 7) pp:1304-1309

Publication Date(Web):

DOI:10.1002/hlca.201000400

Abstract

Isoflavone derivatives were synthesized via intramolecular cyclization of 3-(2-bromophenyl)-3-oxopropanal derivatives, using CuI as the catalyst, 2-picolinic acid (=pyridine-2-carboxylic acid) as the ligand, K₂CO₃ as the base, and DMF as the solvent, in up to 96% yield. The synthesis is functional group-tolerant.

A Novel and Regiospecific Synthesis of 1-Aryl-1H-benzotriazoles via Copper(I)-Catalyzed Intramolecular Cyclization Reaction

Co-reporter:Qi-Lun Liu;Di-Di Wen;Chen-Chen Hang;Qiu-Lian Li

Helvetica Chimica Acta 2010 Volume 93( Issue 7) pp:1350-1354

Publication Date(Web):

DOI:10.1002/hlca.200900384

Abstract

1-Aryl-1H-benzotriazole derivatives were synthesized via intramolecular cyclization of easily obtained triazenes, using CuI as the catalyst, DMSO as the solvent, t-BuONa as the base, and 1,10-phenanthroline as the ligand, in up to 97% yield. The synthesis is regiospecific and functional group-tolerant.

Palladium-catalyzed one-pot synthesis of diazoles via tert-butyl isocyanide insertion

Co-reporter:Xiang-Yuan Fan, Xiao Jiang, Ying Zhang, Zhen-Bang Chen and Yong-Ming Zhu

Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 41) pp:NaN10408-10408

Publication Date(Web):2015/08/19

DOI:10.1039/C5OB01328C

Palladium-catalyzed chemoselective synthesis of indane-1,3-dione derivatives via tert-butyl isocyanide insertion

Co-reporter:Huaqing Duan, Zhong Chen, Li Han, Yulin Feng, Yongming Zhu and Shilin Yang

Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 24) pp:NaN6788-6788

Publication Date(Web):2015/05/11

DOI:10.1039/C5OB00472A

Palladium-catalyzed carbonylative synthesis of isocoumarins and phthalides by using phenyl formate as a carbon monoxide source

Co-reporter:Qing Yuan, Zhen-Bang Chen, Fang-Ling Zhang and Yong-Ming Zhu