Yang-Hui Zhang

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Name: 张扬会; YangHui Zhang

Organization: Tongji University , China

Department: Department of Chemistry

Title: Professor(PhD)

TOPICS

Organic Chemistry

C-H Activation

Chemicals
References

Oxalic acid as the in situ carbon monoxide generator in palladium-catalyzed hydroxycarbonylation of arylhalides

Co-reporter:Changdong Shao;Ailan Lu;Xiaoling Wang;Bo Zhou;Xiaohong Guan;Yanghui Zhang

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 23) pp:5033-5040

Publication Date(Web):2017/06/14

DOI:10.1039/C7OB01052D

An efficient palladium-catalyzed hydroxycarbonylation reaction of arylhalides using oxalic acid as a CO source has been developed. The reaction features high safety, low catalyst loading, and a broad substrate scope, and provides a safe and tractable approach to access a variety of aromatic carboxylic acid compounds. Mechanistic studies revealed the decomposition pattern of oxalic acid.

An approach to spirooxindoles via palladium-catalyzed remote C–H activation and dual alkylation with CH2Br2

Co-reporter:Changdong Shao;Zhuo Wu;Xiaoming Ji;Bo Zhou;Yanghui Zhang

Chemical Communications 2017 vol. 53(Issue 75) pp:10429-10432

Publication Date(Web):2017/09/19

DOI:10.1039/C7CC06196J

A facile and efficient approach for the synthesis of spirooxindoles has been developed via the coupling of spirocyclic C,C-palladacycles with CH2Br2. The key spirocyclic palladacycles are generated catalytically via remote C–H activation. A range of spirooxindoles can be synthesized in good to excellent yields from readily available starting material.

Palladium-Catalyzed Alkylation with Alkyl Halides by C(sp3)−H Activation

Co-reporter:Zhuo Wu;Ding Ma;Bo Zhou;Xiaoming Ji;Xiaotian Ma;Xiaoling Wang; Dr. Yanghui Zhang

Angewandte Chemie International Edition 2017 Volume 56(Issue 40) pp:12288-12291

Publication Date(Web):2017/09/25

DOI:10.1002/anie.201706418

AbstractUtilizing halogens as traceless directing goups represents an attractive strategy for C−H functionalization. A two C−H alkylation system, initiated by the oxidative addition of organohalides to Pd0, has been developed. The first reaction involves an intermolecular alkylation of palladacycles to form C(sp3)−C(sp2) bonds followed by C(sp2)−H activation/cyclization to deliver alkylated benzocyclobutenes as the final products. In the second reaction, two C−C bonds are formed by the reaction of palladacycles with CH2Br2, and provides a facile and efficient method for the synthesis of indanes. The alkylated benzocyclobutene products can be transformed into tricyclic hyrocarbons, and the indane derivatives are essential structural motifs in bioactive and odorant molecules.

Palladium-Catalyzed Alkylation with Alkyl Halides by C(sp3)−H Activation

Co-reporter:Zhuo Wu;Ding Ma;Bo Zhou;Xiaoming Ji;Xiaotian Ma;Xiaoling Wang; Dr. Yanghui Zhang

Angewandte Chemie 2017 Volume 129(Issue 40) pp:12456-12459

Publication Date(Web):2017/09/25

DOI:10.1002/ange.201706418

Palladium-catalyzed C–H alkylation of 2-phenylpyridines with alkyl iodides

Co-reporter:Xiaoling Wang;Xiaoming Ji;Changdong Shao;Yu Zhang;Yanghui Zhang

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 26) pp:5616-5624

Publication Date(Web):2017/07/05

DOI:10.1039/C7OB01232B

Palladium-catalyzed C–H alkylation reaction of 2-phenylpyridines with alkyl iodides has been successfully developed. The palladacycles obtained from 2-phenylpyridines should act as the key intermediates in the alkylation reaction.

Synthesis of Triphenylenes Starting from 2-Iodobiphenyls and Iodobenzenes via Palladium-Catalyzed Dual C–H Activation and Double C–C Bond Formation

Co-reporter:Shulei Pan, Hang Jiang, Yu Zhang, Dushen Chen, and Yanghui Zhang

Organic Letters 2016 Volume 18(Issue 20) pp:5192-5195

Publication Date(Web):October 7, 2016

DOI:10.1021/acs.orglett.6b02071

A novel and facile approach for the synthesis of triphenylenes has been developed via palladium-catalyzed coupling of 2-iodobiphenyls and iodobenzenes. The reaction involves dual palladium-catalyzed C–H activations and double palladium-catalyzed C–C bond formations. A range of unsymmetrically functionalized triphenylenes can be synthesized with the reaction. The approach features readily available starting materials, high atom- and step-economy, and access to various unsymmetrically functionalized triphenylenes.

Synthesis of Fluorenes Starting from 2-Iodobiphenyls and CH2Br2 through Palladium-Catalyzed Dual C–C Bond Formation

Co-reporter:Guangfa Shi, Dushen Chen, Hang Jiang, Yu Zhang, and Yanghui Zhang

Organic Letters 2016 Volume 18(Issue 12) pp:2958-2961

Publication Date(Web):May 27, 2016

DOI:10.1021/acs.orglett.6b01300

A facile and efficient approach is developed for the synthesis of fluorene and its derivatives starting from 2-iodobiphenyls and CH2Br2. A range of fluorene derivatives can be synthesized under relatively mild conditions. The reaction proceeds via a tandem palladium-catalyzed dual C–C bond formation sequence through the key dibenzopalladacyclopentadiene intermediates, which are obtained from 2-iodobiphenyls through palladium-catalyzed C–H activation.

An Approach to Tetraphenylenes via Pd-Catalyzed C–H Functionalization

Co-reporter:Hang Jiang, Yu Zhang, Dushen Chen, Bo Zhou, and Yanghui Zhang

Organic Letters 2016 Volume 18(Issue 9) pp:2032-2035

Publication Date(Web):April 25, 2016

DOI:10.1021/acs.orglett.6b00641

Tetraphenylenes not only are theoretically and experimentally interesting but also have potential applications in a variety of fields such as materials science, supramolecular chemistry, and asymmetric catalysis. A facile and efficient approach is reported for the syntheis of tetraphenylene and its derivatives from 2-iodobiphenyls via Pd-catalyzed C–H activation. A range of substituted tetraphenylenes can be synthesized using this method, and the reaction can be performed on gram scale with relatively high efficiency, demonstrating its practical utility. This novel approach provides easy access to tetraphenylenes and should facilitate research on the application of this type of fascinating molecules.

Sequential Difunctionalization of 2-Iodobiphenyls by Exploiting the Reactivities of a Palladacycle and an Acyclic Arylpalladium Species

Co-reporter:Dushen Chen, Guangfa Shi, Hang Jiang, Yu Zhang, and Yanghui Zhang

Organic Letters 2016 Volume 18(Issue 9) pp:2130-2133

Publication Date(Web):April 26, 2016

DOI:10.1021/acs.orglett.6b00753

A novel sequential difunctionalization reaction of 2-iodobiphenyl has been developed by exploiting the distinct reactivities of a palladacycle and an acyclic arylpalladium species. In this tandem reaction, an in situ formed dibenzopalladacyclopentadiene reacts selectively with an alkyl halide, after which the thus formed acyclic arylpalladium species selectively undergoes a Heck reaction with an alkene. This work demonstrates the strong relationship between the coordination mode of a transition metal complex and its reactivity, which could shed light on the mechanisms of other transition-metal-catalyzed reactions and offer the opportunity to develop other synthetically enabling organic transformations.

Amino acid-promoted C–H alkylation with alkylboronic acids using a removable directing group

Co-reporter:Yu Zhang, Hang Jiang, Dushen Chen and Yanghui Zhang

Organic & Biomolecular Chemistry 2016 vol. 14(Issue 20) pp:4585-4589

Publication Date(Web):26 Apr 2016

DOI:10.1039/C6OB00674D

Palladium-catalyzed C–H alkylation reaction with alkylboronic acids has successfully been developed using a removable pyridyldiisopropylsilyl directing group. The amino acid played a crucial role as a ligand in the reaction. The alkylation protocol is also applicable to the coupling of C(sp3)–H bonds with alkylboronic acids.

Palladium-Catalyzed C–H Ethoxycarbonyldifluoromethylation of Electron-Rich Heteroarenes

Co-reporter:Changdong Shao, Guangfa Shi, Yanghui Zhang, Shulei Pan, and Xiaohong Guan

Organic Letters 2015 Volume 17(Issue 11) pp:2652-2655

Publication Date(Web):May 12, 2015

DOI:10.1021/acs.orglett.5b01024

The first Pd-catalyzed C–H ethoxycarbonyldifluoromethylation with BrCF2CO2Et has been developed. The use of a bidentate phosphine ligand (Xantphos) is critical for the reaction to occur. A variety of electron-rich heteroarenes, including indoles, furans, thiophenes, and pyrroles, can be ethoxycarbonyldifluoromethylated in moderate to excellent yields. The reactions take place at the C–H bonds adjacent to the heteroatoms with high regioselectivity. This method provides a new protocol for the introduction of difuoroalkyl groups into electron-rich heteroarenes.

Silver-Catalyzed C–H Trifluoromethylation of Arenes Using Trifluoroacetic Acid as the Trifluoromethylating Reagent

Co-reporter:Guangfa Shi, Changdong Shao, Shulei Pan, Jingxun Yu, and Yanghui Zhang

Organic Letters 2015 Volume 17(Issue 1) pp:38-41

Publication Date(Web):December 17, 2014

DOI:10.1021/ol503189j

Direct trifluoromethylation of arenes using TFA as the trifluoromethylating reagent was achieved with Ag as the catalyst. This reaction not only provides a new protocol for aryl C–H trifluoromethylation, but the generation of CF3· from TFA may prove useful in other contexts and could potentially be extended to other trifluoromethylation reactions.

Copper-catalyzed amide bond formation from formamides and carboxylic acids

Co-reporter:Hong-Qiang Liu, Jun Liu, Yang-Hui Zhang, Chang-Dong Shao, Jing-Xun Yu

Chinese Chemical Letters 2015 Volume 26(Issue 1) pp:11-14

Publication Date(Web):January 2015

DOI:10.1016/j.cclet.2014.09.007

A highly efficient copper-catalyzed approach to form amide bonds from formamides and carboxylic acids was developed. This protocol shows broad substrate scopes and high yields in the presence of 1 mol% catalyst and 4.0 equiv. formamides.A highly efficient copper-catalyzed approach to form amide bonds from formamides and carboxylic acids was developed. This protocol shows broad substrate scopes and high yields in the presence of 1 mol% catalyst and 4.0 equiv. formamides.

Ligand-Promoted Oxidative Cross-Coupling of Aryl Boronic Acids and Aryl Silanes by Palladium Catalysis

Co-reporter:Jingxun Yu;Jun Liu;Guangfa Shi;Changdong Shao ;Dr. Yanghui Zhang

Angewandte Chemie 2015 Volume 127( Issue 13) pp:4151-4154

Publication Date(Web):

DOI:10.1002/ange.201412288

Abstract

The first cross-coupling reaction between aryl silanes and aryl boronic acids is described. This transformation represents one of the very few examples of coupling reactions between two nucleophilic organometallic reagents and provides a new method for the formation of biaryl compounds. The successful development of this reaction was enabled by the use of commercially available 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) as the ligand. A small amount of BINAP (3 mol %) was sufficient to suppress the formation of the homocoupling products, and the reaction yielded the cross-coupling products with high selectivity under mild conditions, even when the ratio of the two coupling partners was 1:1.

Ligand-Promoted Oxidative Cross-Coupling of Aryl Boronic Acids and Aryl Silanes by Palladium Catalysis

Co-reporter:Jingxun Yu;Jun Liu;Guangfa Shi;Changdong Shao ;Dr. Yanghui Zhang

Angewandte Chemie International Edition 2015 Volume 54( Issue 13) pp:4079-4082

Publication Date(Web):

DOI:10.1002/anie.201412288

Abstract

Carboxylate-Directed CH Functionalization

Co-reporter:Guangfa Shi;Yanghui Zhang

Advanced Synthesis & Catalysis 2014 Volume 356( Issue 7) pp:1419-1442

Publication Date(Web):

DOI:10.1002/adsc.201400028

Copper-catalyzed highly efficient ester formation from carboxylic acids/esters and formates

Co-reporter:Jun Liu, Changdong Shao, Yanghui Zhang, Guangfa Shi and Shulei Pan

Organic & Biomolecular Chemistry 2014 vol. 12(Issue 17) pp:2637-2640

Publication Date(Web):06 Mar 2014

DOI:10.1039/C4OB00193A

A highly efficient copper-catalyzed protocol for the synthesis of esters has been developed from formates. This protocol is applicable to reactions with either esters or acids as the substrates, and shows broad substrate scopes and high yields.

Copper-Catalyzed Decarboxylative Methylation of Aromatic Carboxylic Acids with PhI(OAc)2

Co-reporter:Yuyu Jiang;Shulei Pan;Yanghui Zhang;Jingxun Yu;Hongqiang Liu

European Journal of Organic Chemistry 2014 Volume 2014( Issue 10) pp:2027-2031

Publication Date(Web):

DOI:10.1002/ejoc.201301815

Abstract

The copper-catalyzed decarboxylative methylation of aromatic carboxylic acids was developed by using PhI(OAc)₂ to provide a new strategy for the methylation of aryl acids through the decarboxylation of alkyl acids. The mechanism and the roles of each reactant in the reaction were investigated extensively.

Palladium-Catalyzed Benzylation of Carboxylic Acids with Toluene via Benzylic C–H Activation

Co-reporter:Hongqiang Liu, Guangfa Shi, Shulei Pan, Yuyu Jiang, and Yanghui Zhang

Organic Letters 2013 Volume 15(Issue 16) pp:4098-4101

Publication Date(Web):July 29, 2013

DOI:10.1021/ol401687f

Direct benzylation of carboxylic acids with toluene has been developed via palladium-catalyzed C–H acyloxylation under 1 atm of oxygen. This reaction demonstrates good functional group tolerance and high yields, providing a facile, atom-economic, and efficient method for the synthesis of benzyl esters.

Oxalic acid as the in situ carbon monoxide generator in palladium-catalyzed hydroxycarbonylation of arylhalides

Co-reporter:Changdong Shao, Ailan Lu, Xiaoling Wang, Bo Zhou, Xiaohong Guan and Yanghui Zhang

Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 23) pp:NaN5040-5040

Publication Date(Web):2017/05/22

DOI:10.1039/C7OB01052D

Amino acid-promoted C–H alkylation with alkylboronic acids using a removable directing group

Co-reporter:Yu Zhang, Hang Jiang, Dushen Chen and Yanghui Zhang

Organic & Biomolecular Chemistry 2016 - vol. 14(Issue 20) pp:NaN4589-4589

Publication Date(Web):2016/04/26

DOI:10.1039/C6OB00674D

Copper-catalyzed highly efficient ester formation from carboxylic acids/esters and formates

Co-reporter:Jun Liu, Changdong Shao, Yanghui Zhang, Guangfa Shi and Shulei Pan