Xiao-dong Jia

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Name: 贾晓东; Jia, XiaoDong

Organization: Yangzhou University , China

Department: College of Chemistry and Chemical Engineering

Title: Professor(PhD)

TOPICS

Organic Chemistry

Chemicals
References

Active sp3 C–H Bond Oxidation Initiated sp3–sp2 Consecutive C–H Functionalization of N-Arylglycine Amides: Construction of Isatins

Co-reporter:Honghe Ji, Yingzu Zhu, Yu Shao, Jing Liu, Yu Yuan, and Xiaodong Jia

The Journal of Organic Chemistry September 15, 2017 Volume 82(Issue 18) pp:9859-9859

Publication Date(Web):August 17, 2017

DOI:10.1021/acs.joc.7b01480

In the presence of catalytic triarylamine radical cation, an sp3–sp2 consecutive C–H functionalization of N-arylglycine amides was achieved, providing a series of isatin derivatives in high yields. In this transformation, the initial aerobic oxidation of the relatively active sp3 C–H bonds triggered the following intramolecular cyclization, in which the aniline group was employed as a removable auxiliary group to enable the consecutive process.

Oxidative Phosphorylation of N-Aryl Glycine Amides via sp3 C−H Functionalization

Co-reporter:Xiaodong Jia;Xiaofei Liu;Yu Shao;Yu Yuan;Yingzu Zhu;Wentao Hou;Xuewen Zhang

Advanced Synthesis & Catalysis 2017 Volume 359(Issue 24) pp:4399-4404

Publication Date(Web):2017/12/19

DOI:10.1002/adsc.201700850

AbstractAn efficient phosphorylation of various glycine amides has been developed for radical cation salt-induced C−H functionalization, producing a series of α-aminophosphonates in high yields. Different from reported approaches, trialkyl phosphite was chosen as the phosphorus nucleophile, and the scope investigation shows broad functional group tolerance and high efficiency of the oxidative phosphorylation. This method provides a new way to synthesize α-aminophosphonates.

Highly selective sp3 C–N bond activation of tertiary anilines modulated by steric and thermodynamic factors

Co-reporter:Xiaodong Jia;Pengfei Li;Yu Shao;Yu Yuan;Honghe Ji;Wentao Hou;Xiaofei Liu;Xuewen Zhang

Green Chemistry (1999-Present) 2017 vol. 19(Issue 23) pp:5568-5574

Publication Date(Web):2017/11/27

DOI:10.1039/C7GC02775C

A highly selective sp3 C–N cleavage of tertiary anilines was achieved using the TBN/TEMPO catalyst system. When N,N-diaklylanilines (alkyl, benzyl) were employed, the N–CH3 bond was selectively cleaved via radical C–H activation. Moreover, when the allyl group was installed, totally reverse selectivity was observed. It is worth noting that the solvent effect is also crucial to obtain high reaction efficiency and selectivity.

A dual removable activating group enabled the Povarov reaction of N-arylalanine esters: synthesis of quinoline-4-carboxylate esters

Co-reporter:Xiaodong Jia;Shiwei Lü;Yu Yuan;Xuewen Zhang;Liang Zhang;Liangliang Luo

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 14) pp:2931-2937

Publication Date(Web):2017/04/05

DOI:10.1039/C7OB00446J

A dual removable activating group enabled Povarov reaction of N-arylalanine esters was reported. N-Arylalanine ester was utilized as the sole carbon source to generate N-arylimine and its tautomer, enamine, in situ by aerobic oxidation of sp3 C–H bonds, and then the consecutive reaction delivered the desired quinoline-4-carboxylate esters in high yields.

C–H Activation Relay (CHAR): An Efficient Construction of Isatin Skeleton by Aerobic Oxidation of Glycine Esters

Co-reporter:Xiaodong Jia, Yingzu Zhu, Yu Yuan, Xuewen Zhang, Shiwei Lü, Liang Zhang, and Liangliang Luo

ACS Catalysis 2016 Volume 6(Issue 9) pp:6033

Publication Date(Web):August 8, 2016

DOI:10.1021/acscatal.6b01781

Directed by the strategy of C–H activation relay (CHAR), an efficient construction of isatin skeleton was developed through catalytic oxidation of glycine esters. The mechanistic study reveals that the oxidation of the relatively active C–H bonds initiated the followed activation of remote and inert C–H bonds, and an intramolecular 1,6-hydrogen shift was involved as a key step.Keywords: 1,6-hydrogen shift; aerobic oxidation; C−H activation; glycine ester; isatin

What Happens When the Terminal Aromatization is Blocked? Construction of 1,2-Dihydroquinoline Derivatives by sp3 CH Bond Oxidation of N-Arylalaninates

Co-reporter:Shiwei Lü;Yingzu Zhu;Xingge Ma ;Xiaodong Jia

Advanced Synthesis & Catalysis 2016 Volume 358( Issue 7) pp:1004-1010

Publication Date(Web):

DOI:10.1002/adsc.201500885

An Unexpected Construction of 2-Arylquinolines from N-Cinnamylanilines through sp3 CH Aerobic Oxidation Induced by a Catalytic Radical Cation Salt

Co-reporter:Fang Liu;Liangliang Yu;Shiwei Lv;Junjun Yao;Jing Liu ;Xiaodong Jia

Advanced Synthesis & Catalysis 2016 Volume 358( Issue 3) pp:459-465

Publication Date(Web):

DOI:10.1002/adsc.201500574

Carbonylation of Csp3H Bonds through Oxidative Wittig-Type Reaction: An Unprecedented Version of Wittig Reaction

Co-reporter:Yingzu Zhu;Shiwei Lü;Xingge Ma;Liang Zhang;Liangliang Luo ;Dr. Xiaodong Jia

Asian Journal of Organic Chemistry 2016 Volume 5( Issue 5) pp:617-620

Publication Date(Web):

DOI:10.1002/ajoc.201600055

Abstract

A Wittig-type reaction was achieved by radical cation salt induced aerobic oxidation of Csp³−H bonds. Different from the “standard” version of the Wittig reaction, in which a carbon-carbon double bond is formed from a carbonyl, carbonyl groups can be installed by similar process.

Cover Picture: Carbonylation of Csp3H Bonds through Oxidative Wittig-Type Reaction: An Unprecedented Version of Wittig Reaction (Asian J. Org. Chem. 5/2016)

Co-reporter:Yingzu Zhu;Shiwei Lü;Xingge Ma;Liang Zhang;Liangliang Luo ;Dr. Xiaodong Jia

Asian Journal of Organic Chemistry 2016 Volume 5( Issue 5) pp:

Publication Date(Web):

DOI:10.1002/ajoc.201600127

An aerobic oxidative aza-[4+2] cycloaddition induced by radical cation salt: Synthesis of dihydroquinazoline derivatives

Co-reporter:Liangliang Luo, Xiaolong Zhao, Liang Zhang, Yu Yuan, Shiwei Lü, Xiaodong Jia

Tetrahedron Letters 2016 Volume 57(Issue 51) pp:5830-5833

Publication Date(Web):21 December 2016

DOI:10.1016/j.tetlet.2016.11.052

•The catalytic oxidation of sp3 CH bonds in glycines was achieved.•The aerobic oxidation is promoted by triarylamine radical cation salt.•A series of functionalized quinazolines were synthesized in good yields.A facile and efficient radical cation salt-induced approach to dihydroquinazoline derivatives has been developed by sp3 CH oxidation, and the method uses readily available glycine esters as the starting material under aerobic oxidation conditions without addition of any additive. The present method provides a convenient and practical route for construction of quinazoline skeleton.

Oxidative Povarov Reaction via sp3 C–H Oxidation of N-Benzylanilines Induced by Catalytic Radical Cation Salt: Synthesis of 2,4-Diarylquinoline Derivatives

Co-reporter:Jing Liu, Fang Liu, Yingzu Zhu, Xingge Ma, and Xiaodong Jia

Organic Letters 2015 Volume 17(Issue 6) pp:1409-1412

Publication Date(Web):March 10, 2015

DOI:10.1021/acs.orglett.5b00244

Oxidative Povarov reaction of N-benzylanilines was realized under catalytic radical cation salt induced conditions. The mechanism studies revealed that a radical intermediate was involved in this catalytic oxidation. This method provides a new way to synthesize 2,4-diarylquinoline derivatives.

Radical Cation Salt-Promoted Catalytic Aerobic sp3 C–H Oxidation: Construction of Quinoline-Fused Lactones and Lactams

Co-reporter:Yaxin Wang, Fangfang Peng, Jing Liu, Congde Huo, Xicun Wang, and Xiaodong Jia

The Journal of Organic Chemistry 2015 Volume 80(Issue 1) pp:609-614

Publication Date(Web):December 3, 2014

DOI:10.1021/jo502184k

A direct construction of quinoline-fused lactones and lactams was achieved by sp3 C–H bond oxidation of N-aryl glycine esters and amides under catalytic radical cation salt-induced conditions. These polycyclic products are formed in a single step from readily accessible starting materials, and this method provides a new synthetic approach to this class of heterocycles.

Cerium(IV)-Catalyzed sp3 CH Bond Oxidation of Glycine Derivatives: Radical Cation Prompted Dioxygen Activation in the Presence of Triarylamine

Co-reporter:Jing Liu;Yaxin Wang;Liangliang Yu;Congde Huo;Xicun Wang ;Xiaodong Jia

Advanced Synthesis & Catalysis 2014 Volume 356( Issue 14-15) pp:3214-3218

Publication Date(Web):

DOI:10.1002/adsc.201400005

Catalytic Oxidation of C(sp3)H Bonds Induced by a Radical Cation Salt: Construction of 1,4-Dihydropyridines Using a Fragment-Reassembly Strategy

Co-reporter:Xiaodong Jia;Yaxin Wang;Fangfang Peng;Congde Huo;Liangling Yu;Jing Liu ;Xicun Wang

Advanced Synthesis & Catalysis 2014 Volume 356( Issue 6) pp:1210-1216

Publication Date(Web):

DOI:10.1002/adsc.201300810

Catalytic aromatization of 1,4-dihydropyridines by radical cation salt prompted aerobic oxidation

Co-reporter:Xiaodong Jia, Liangliang Yu, Congde Huo, Yaxin Wang, Jing Liu, Xicun Wang

Tetrahedron Letters 2014 Volume 55(Issue 1) pp:264-266

Publication Date(Web):1 January 2014

DOI:10.1016/j.tetlet.2013.11.010

Aromatization of Hantzch 1,4-dihydropyridines was achieved under radical cation salt induced conditions, in which triarylamine radical cation acts as an efficient catalyst to prompt the aerobic oxidation of 1,4-DHPs in a catalytic way.

Synthesis of 2,3-disubstituted quinolines from in situ generated imines and its enamine tautomer under radical cation induced conditions

Co-reporter:Xiaodong Jia, Fangfang Peng, Chang Qing, Congde Huo, Yaxin Wang, Xicun Wang

Tetrahedron Letters 2013 Volume 54(Issue 36) pp:4950-4952

Publication Date(Web):4 September 2013

DOI:10.1016/j.tetlet.2013.07.014

A tandem cyclization/aromatization of anilines and aldehydes was achieved under catalytic radical cation salt induced conditions, producing a series of 2,3-disubstituted quinolines in good yields. In this reaction, the in situ generated imine tautomerizes to enamine, which acts as a dienophile to participate in the tandem cyclization, and further elimination of the anilino group triggers the aromatization of tetrahydroquinolines, avoiding harsh conditions.

Catalytic sp3 C–H Oxidation of Peptides and Their Analogues by Radical Cation Salts: From Glycine Amides to Quinolines

Co-reporter:Xiaodong Jia, Yaxin Wang, Fangfang Peng, Congde Huo, Liangliang Yu, Jing Liu, and Xicun Wang

The Journal of Organic Chemistry 2013 Volume 78(Issue 18) pp:9450-9456

Publication Date(Web):August 16, 2013

DOI:10.1021/jo401018v

A catalytic α-sp3 C–H oxidation of peptides and glycine amides was achieved under radical cation salt catalysis in the presence of O2, producing a series of substituted quinolines. The scope of this reaction shows good functional group tolerance and high efficiency of the oxidative functionalization.

Catalytic Radical Cation Salt Induced Csp3–H Functionalization of Glycine Derivatives: Synthesis of Substituted Quinolines

Co-reporter:Xiaodong Jia, Fangfang Peng, Chang Qing, Congde Huo, and Xicun Wang

Organic Letters 2012 Volume 14(Issue 15) pp:4030-4033

Publication Date(Web):July 19, 2012

DOI:10.1021/ol301909g

A domino Csp3–H functionalization of glycine derivatives was achieved under catalytic radical cation salt induced conditions, producing a series of quinolines. The proposed mechanism shows that a peroxyl radical cation, which is generated by the coupling between O2 and TBPA+•, might be involved to initiate the catalytic oxidation.

Radical cation salt induced Povarov reaction between iminoethyl glyoxylate and N-vinylamides: synthesis of quinoline-2-carboxylate derivatives

Co-reporter:Xiaodong Jia, Chang Qing, Congde Huo, Fangfang Peng, Xicun Wang

Tetrahedron Letters 2012 Volume 53(Issue 52) pp:7140-7142

Publication Date(Web):26 December 2012

DOI:10.1016/j.tetlet.2012.10.097

A domino process between iminoethyl glyoxylate and N-vinylamides was achieved under the catalytic radical cation salt induced conditions, producing a series of quinoline-2-carboxylates. N-Vinylamides were involved as an acetylene equivalent. A possible mechanism was proposed to rationalize the formation of the products.

Cross double Mannich reaction catalyzed by I2: Synthesis of highly substituted 4-piperidones

Co-reporter:Xiao Dong Jia, Xiang Ning Chen, Cong De Huo, Fang Fang Peng, Chang Qing, Xi Cun Wang

Chinese Chemical Letters 2012 Volume 23(Issue 3) pp:309-312

Publication Date(Web):March 2012

DOI:10.1016/j.cclet.2011.12.008

Cross double Mannich reaction and tandem cyclization were achieved under iodine catalyzed conditions, yielding a series of highly substituted 4-piperidones. Among the possible diastereomers, only one diastereomer was isolated, which could be ascribed to the chair-like transition state in six-membered ring, in which all of the hindered groups are located in the pseudoequatorial orientation.

Double Mannich Reaction and Tandem Cyclization of Imines with Ketones Catalyzed by Indium(III) Chloride Tetrahydrate: Stereoselective Synthesis of Highly Substituted 4-Piperidones

Co-reporter:Xiao-Dong Jia;Wen-Juan Wang;Cong-De Huo;Yan Ren;Xiang-Ning Chen;Xiao-Lan Xu;Xi-Cun Wang

Advanced Synthesis & Catalysis 2011 Volume 353( Issue 2-3) pp:315-319

Publication Date(Web):

DOI:10.1002/adsc.201000760

Abstract

A double Mannich reaction followed by tandem cyclization of imines and ketones catalyzed by indium(III) chloride tetrahydrate (InCl₃⋅4 H₂O) was investigated, and a series of 1,2,6-triaryl-4-piperidones was synthesized in a stereoselective way. In this reaction, aromatic imines substituted by electron-withdrawing groups exhibited high reactivity toward the cyclization to 4-piperidones. A variety of ketones are tolerated in this tandem process, including those that are sterically encumbered.

I2-Induced Stereospecific Synthesis of 4-Piperidones through Double Mannich Reaction and Tandem Cyclization

Co-reporter:Xiao-Dong Jia;Xiang-Ning Chen;Xiao-E Wang;Cong-De Huo;Wen-Juan Wang;Yan Ren ;Xi-Cun Wang

European Journal of Organic Chemistry 2011 Volume 2011( Issue 9) pp:1627-1631

Publication Date(Web):

DOI:10.1002/ejoc.201001607

Abstract

An I₂-induced double Mannich reaction and tandem cyclization of imines and ketones was investigated for the synthesis of a series of 1,2,6-triaryl-4-piperidones. During the process of cyclization, only one product was produced out of four possible 4-piperidones. Two pathways involving the balance between chelation effects and hydrogen bonding were proposed to rationalize the formation of the products, which was supported by further investigation of the reaction between β-aminoketones and imines.

Synthesis of β-Aminoketones and Construction of Highly Substituted 4-Piperidones by Mannich Reaction Induced by Persistent Radical Cation Salts

Co-reporter:Xiao-Dong Jia, Xiao-E Wang, Cai-Xia Yang, Cong-De Huo, Wen-Juan Wang, Yan Ren and Xi-Cun Wang

Organic Letters 2010 Volume 12(Issue 4) pp:732-735

Publication Date(Web):January 20, 2010

DOI:10.1021/ol9027978

A Mannich reaction of imines and ketones induced by persistent radical cation salts was investigated, and a series of Mannich bases, β-aminoketones, were synthesized. A novel cyclization to form the 4-piperidone skeleton was achieved in a tandem process. The reaction can be rationalized as a radical cation process supported by various evidence.

Radical cation salt induced tandem cyclization between anilines and N-vinyl amides: synthesis of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinoline derivatives

Co-reporter:Xiao-dong Jia, Yan Ren, Cong-de Huo, Wen-Juan Wang, Xiang-Ning Chen, Xiao-Lan Xu, Xi-cun Wang

Tetrahedron Letters 2010 Volume 51(Issue 51) pp:6779-6782

Publication Date(Web):22 December 2010

DOI:10.1016/j.tetlet.2010.10.106

A tandem cyclization of imines with N-vinyllactams induced by TBPA+ was investigated, and a series of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinolines were synthesized based on a domino process in which N-vinyllactams serve as an acetaldehyde surrogate. A single electron transfer mechanism was proposed and radical cation salt acts as both a Lewis acid and one electron oxidant to induce such transformation.Tandem cyclization of imines and N-vinyllactams induced by TBPA+ was investigated and a series of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinolines were synthesized based on a domino process in which N-vinyllactams serve as an acetaldehyde equivalent. A single electron transfer mechanism was proposed and radical cation salt acts as both a Lewis acid and one electron oxidant to induce such transformation.

Synthesis of oxime ethers under single electron oxidation induced by radical cation tris(aryl)aminium salts: O-alkylation of oximes with n-vinyl lactams

Co-reporter:Xiaodong Jia, Xiaoe Wang, Caixia Yang, Yuxia Da, Li Yang, Zhongli Liu

Tetrahedron 2009 65(11) pp: 2334-2338

Publication Date(Web):

DOI:10.1016/j.tet.2009.01.025

A dual removable activating group enabled the Povarov reaction of N-arylalanine esters: synthesis of quinoline-4-carboxylate esters

Co-reporter:Xiaodong Jia, Shiwei Lü, Yu Yuan, Xuewen Zhang, Liang Zhang and Liangliang Luo

Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 14) pp:NaN2937-2937

Publication Date(Web):2017/03/08

DOI:10.1039/C7OB00446J