Xianxiu Xu

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Name: 徐显秀

Organization: Northeast Normal University , China

Department: Department of Chemistry

Title: NULL(PhD)

TOPICS

Organic Chemistry

Fluorination

Chemicals
References

Chemistry of Ketene N,S-Acetals: An Overview

Co-reporter:Lin Zhang, Jinhuan Dong, Xianxiu Xu, and Qun Liu

Chemical Reviews 2016 Volume 116(Issue 2) pp:287

Publication Date(Web):January 13, 2016

DOI:10.1021/acs.chemrev.5b00360

Push–pull alkenes, which bear electron-donating and -accepting group(s) at both termini of a C═C double bond, respectively, are of interest not only for their unique electronic properties but also for their importance as versatile building blocks in organic synthesis. In the world of ketene acetals having the push–pull alkene skeleton, ketene N,S-acetal is most likely the biggest family according to the number and types of these compounds. The first ketene N,S-acetal compound was reported in 1956. As a cyclic ketene N,S-acetal compound, nithiazine, the first lead structure of neonicotinoid insecticides, was reported in 1978. The characteristics of ketene N,S-acetals, which have the structural feature of ketene S,S-acetals and enaminones, make them versatile and easy to use, especially in cyclization and multicomponent reactions for the synthesis of various heterocyclic systems and related natural products. There has been an increasing wealth of information about the synthesis and synthetic applications of ketene N,S-acetals, especially, in recent years. This review provides comprehensive knowledge on the chemistry of ketene N,S-acetals.

Diastereoselective Synthesis of 3,4-Benzomorphan Derivatives via Tandem [5 + 1]/Hemiaminalization of (2-Aminoaryl)divinyl Ketones

Co-reporter:Yifei Li; Chengjie Feng; Hui Shi

Organic Letters 2016 Volume 18(Issue 2) pp:324-327

Publication Date(Web):January 6, 2016

DOI:10.1021/acs.orglett.5b03506

A novel tandem formal [5 + 1]/hemiaminalization reaction based on the readily available (2-aminoaryl)divinyl ketones and various nucleophiles has been developed. The reaction represents a highly efficient and convenient methodology for the synthesis of 3,4-benzomorphan derivatives with high diastereoselectivity, and three new bonds and two rings are successively formed in one step under mild, metal-free conditions.

Accessing benzo[f]indole-4,9-diones via a ring expansion strategy: silver-catalyzed tandem reaction of tosylmethyl isocyanide (TosMIC) with 2-methyleneindene-1,3-diones

Co-reporter:Lingjuan Zhang, Xueming Zhang, Zhengchang Lu, Dawei Zhang, Xianxiu Xu

Tetrahedron 2016 Volume 72(Issue 49) pp:7926-7930

Publication Date(Web):8 December 2016

DOI:10.1016/j.tet.2016.10.015

A silver-catalyzed tandem reaction of TosMIC with 2-methyleneindene-1,3-diones was developed for the direct synthesis of benzo[f]indole-4,9-diones. In this reaction, a domino [3+2]-cycloaddition/imidoyl anion cyclization/ring opening of cyclopropanolate/aromatization is proposed and three CC bonds are formed successively.

Kinetic Control of Rh(III)-Catalyzed Annulation of C–H Bonds with Quinones: Chemoselective Synthesis of Hydrophenanthridinones and Phenanthridinones

Co-reporter:Wei Yang, Jingyi Wang, Zhonglin Wei, Qian Zhang, and Xianxiu Xu

The Journal of Organic Chemistry 2016 Volume 81(Issue 4) pp:1675-1680

Publication Date(Web):February 5, 2016

DOI:10.1021/acs.joc.5b02903

A temperature-dependent redox-neutral Rh(III)-catalyzed C–H bond annulation of N-methoxybenzamides with quinones was developed for the chemoselective synthesis of hydrophenanthridinones and phenanthridinones. This reaction involves an Rh(III)-catalyzed C–H bond functionalization and a subsequent cyclization through the directing group nucleophilic addition to the carbonyl group at room temperature.

Expedient and Divergent Tandem One-Pot Synthesis of Benz[e]indole and Spiro[indene-1,3′-pyrrole] Derivatives from Alkyne-Tethered Chalcones/Cinnamates and TosMIC

Co-reporter:Xue Zhang, Chengjie Feng, Tao Jiang, Yifei Li, Ling Pan, and Xianxiu Xu

Organic Letters 2015 Volume 17(Issue 14) pp:3576-3579

Publication Date(Web):July 8, 2015

DOI:10.1021/acs.orglett.5b01676

An efficient solvent-dependent regioselective [3 + 2]-cycloaddition/iodocyclization cascade reaction of alkyne-tethered chalcones/cinnamates and TosMIC has been developed. The reaction represents a novel protocol for the expedient and divergent one-pot synthesis of benz[e]indoles and spiro[indene-1,3′-pyrroles] from acyclic common precursors at room temperature.

Rh(III)-catalyzed oxidative C–H bond arylation with hydroquinones: sustainable synthesis of dibenzo[b,d]pyran-6-ones and benzo[d]naphtho[1,2-b]pyran-6-ones

Co-reporter:Wei Yang, Shan Wang, Qian Zhang, Qun Liu and Xianxiu Xu

Chemical Communications 2015 vol. 51(Issue 4) pp:661-664

Publication Date(Web):14 Nov 2014

DOI:10.1039/C4CC08260E

An efficient Rh(III)-catalyzed C–H bond arylation with phenol derivatives was developed for the direct and sustainable synthesis of dibenzo[b,d]pyran-6-ones and benzo[d]naphtho[1,2-b]pyran-6-ones. This reaction shows good substrate scope and excellent functional group compatibility and gives the products in good yields with excellent chemoselectivity.

Rhodium(III)-catalyzed intramolecular amidoarylation and hydroarylation of alkyne via C–H activation: switchable synthesis of 3,4-fused tricyclic indoles and chromans

Co-reporter:Xue Zhang, Yifei Li, Hui Shi, Lunan Zhang, Shanshan Zhang, Xianxiu Xu and Qun Liu

Chemical Communications 2014 vol. 50(Issue 55) pp:7306-7309

Publication Date(Web):21 May 2014

DOI:10.1039/C4CC02398F

The controllable intramolecular amidoarylation and hydroarylation of alkynes has been achieved via rhodium(III)-catalyzed C–H activation. The merger of two distinct reaction pathways allows for the development of atom- and step-economic protocols for the switchable synthesis of 3,4-fused indoles and chromans, respectively.

[3 + 3]-Cycloaddition Reactions of α-Acidic Isocyanides with 1,3-Dipolar Azomethine Imines

Co-reporter:Juan Du, Xianxiu Xu, Yifei Li, Ling Pan, and Qun Liu

Organic Letters 2014 Volume 16(Issue 15) pp:4004-4007

Publication Date(Web):July 23, 2014

DOI:10.1021/ol501829k

α-Acidic isocyanides are versatile reagents in organic synthesis, especially for the synthesis of five-membered heterocycles via [3 + 2]-cycloaddition reactions with activated multiple bonds. In this communication, the first [3 + 3]-cross-cycloaddition of α-acidic isocyanides with 1,3-dipolar azomethine imines to generate a series of 1,2,4-triazine derivatives with significant regiochemical control under mild catalytic reaction conditions is described. This new strategy shows that α-acidic isocyanides can also be taken as potent reagents for the synthesis of six-membered heterocycles through [3 + 3]-cross-cycloaddition reactions with 1,3-dipoles.

Hydroxyamination of aryl C–H bonds with N-hydroxycarbamate by synergistic Rh/Cu catalysis at room temperature

Co-reporter:Wei Yang, Jiaqiong Sun, Xianxiu Xu, Qian Zhang and Qun Liu

Chemical Communications 2014 vol. 50(Issue 34) pp:4420-4422

Publication Date(Web):13 Jan 2014

DOI:10.1039/C3CC49496A

A novel hydroamination of aryl C–H bonds has been accomplished using N-Boc-hydroxyamine via synergistic combination of rhodium and copper catalysis. The merger of two robust catalytic systems has allowed for the development of a mild and sustainable protocol for the direct formation of benzo[c]isoxazol-3(1H)-ones.

Aerobic copper-catalyzed oxidative [6C+1C] annulation: an efficient route to seven-membered carbocycles

Co-reporter:Xiao Liu, Lingjuan Zhang, Xianxiu Xu, Shan Wang, Ling Pan, Qian Zhang and Qun Liu

Chemical Communications 2014 vol. 50(Issue 63) pp:8764-8767

Publication Date(Web):19 Jun 2014

DOI:10.1039/C4CC03095H

It has been revealed for the first time that co-promoted by CuCl and NaH in the presence of molecular oxygen (air), the reaction of dicinnamoyl ketene dithioacetals as the acyclic C6 synthons with ethyl cyanoacetate gives functionalized seven-membered carbocycles. A mechanism is proposed involving a tandem Michael addition–intramolecular radical cyclization–benzyl C(sp3)–H bond oxidation.

Direct Synthesis of Pyrrolo[3,4-c]quinolines from the Domino Reaction of Tosylmethyl Isocyanides and Aminochalcones

Co-reporter:Zhongyan Hu;Yifei Li;Ling Pan

Advanced Synthesis & Catalysis 2014 Volume 356( Issue 14-15) pp:2974-2978

Publication Date(Web):

DOI:10.1002/adsc.201400468

Bicyclization of Isocyanides with Alkenoyl Bis(ketene dithioacetals): Access to 6,7-Dihydro-1H-indol-4(5H)-ones

Co-reporter:Yifei Li, Xianxiu Xu, Hui Shi, Ling Pan, and Qun Liu

The Journal of Organic Chemistry 2014 Volume 79(Issue 12) pp:5929-5933

Publication Date(Web):May 20, 2014

DOI:10.1021/jo500928c

The tandem [3 + 2] cycloaddition/intramolecular imidoyl anion trapping strategy has been successfully applied for the synthesis of 6,7-dihydro-1H-indol-4(5H)-ones from alkenoyl bis(ketene dithioacetals) and tosylmethyl isocyanide. The reaction proceeded smoothly under mild reaction conditions to afford bicyclization products in high to excellent yields in a single step.

Tandem Michael addition/isocyanide insertion into the C–C bond: a novel access to 2-acylpyrroles and medium-ring fused pyrroles

Co-reporter:Lingjuan Zhang, Xianxiu Xu, Qiu-rong Shao, Ling Pan and Qun Liu

Organic & Biomolecular Chemistry 2013 vol. 11(Issue 42) pp:7393-7399

Publication Date(Web):24 Sep 2013

DOI:10.1039/C3OB41793J

A new reaction model, tandem Michael addition/formal isocyanide insertion into the acyl C–C bond, has been developed. Thus, a series of 2-acylpyrroles and seven-/eight-membered ring fused pyrroles were synthesized from the reaction of methyl isocyanides with enones in a single operation.

Double nucleophilic attack on isocyanide carbon: a synthetic strategy for 7-aza-tetrahydroindoles

Co-reporter:Yifei Li, Xianxiu Xu, Chunyu Xia, Lingjuan Zhang, Ling Pan and Qun Liu

Chemical Communications 2012 vol. 48(Issue 100) pp:12228-12230

Publication Date(Web):31 Oct 2012

DOI:10.1039/C2CC35896D

A novel and efficient route for the synthesis of 7-aza-tetrahydroindoles from N-aryl/alkyl-alkenoylacetamides and ethyl isocyanoacetate is described. A mechanism, involving a stepwise [3+2] cycloaddition–intramolecular aza-Michael addition cascade, is proposed that explains the origin of the double nucleophilic attack on the isocyanide carbon atom.

Dithiolane-Directed Tandem Oxidation/1,2-Benzyl Migration of Tetramic Acids under Ambient Conditions

Co-reporter:Yifei Li;Chunyu Xia;Ling Pan ;Qun Liu

Advanced Synthesis & Catalysis 2012 Volume 354( Issue 9) pp:1712-1716

Publication Date(Web):

DOI:10.1002/adsc.201200096

Abstract

Reactions directly involving triplet oxygen are an important issue in organic and biological chemistry. We now report that exposure of tetramic acids in the open air (molecular oxygen) at room temperature can lead to the formation of succinimide derivatives in high to excellent yields via tandem oxidation/1,2-benzyl migration. In this reaction, the dithiolane moiety plays a crucial role and succinimides are produced either in the presence or absence of dibutyl sulfide as reductant.

Double Isocyanide Cyclization: A Synthetic Strategy for Two-Carbon-Tethered Pyrrole/Oxazole Pairs

Co-reporter:Yifei Li ; Xianxiu Xu ; Jing Tan ; Chunyu Xia ; Dawei Zhang ;Qun Liu

Journal of the American Chemical Society 2011 Volume 133(Issue 6) pp:1775-1777

Publication Date(Web):January 18, 2011

DOI:10.1021/ja110864t

A new strategy for the construction of the compounds with two different heterocycles, linked by a C2-tether via a domino process involving [5 + 1] annulation, ring-opening, and subsequent double isocyanide cyclization, from the reaction of ethyl isocyanoacetate with divinyl ketones (DVKs) has been developed. The chemoselective fragmentation of the cyclohexanone intermediate is the key for the formation of not only the C2-tether but also the two different heterocycles.

Bicyclization of Isocyanides: A Synthetic Strategy for Fused Pyrroles

Co-reporter:Lingjuan Zhang;Wenming Xia ;Qun Liu

Advanced Synthesis & Catalysis 2011 Volume 353( Issue 14-15) pp:2619-2623

Publication Date(Web):

DOI:10.1002/adsc.201100501

Abstract

On the isocyanide carbon atom, two CC sigma bonds are formed in the bicyclization reaction of the readily available acyclic substrates with tosylmethyl isocyanides. The reaction can proceed under extremely mild and metal-free conditions to give the products in high to excellent yields. The powerful potential of this strategy deserves attention because it is a new paradigm for trapping of the incipient imidoyl anion, by a carbon electrophile instead of a proton.

Direct Synthesis of 6-Azabicyclo[3.2.1]oct-6-en-2-ones and Pyrrolizidines from Divinyl Ketones and Observation of Remarkable Substituent Effects

Co-reporter:Xianxiu Xu;Yifei Li;Yu Zhang;Lingjuan Zhang;Ling Pan ;Qun Liu

Advanced Synthesis & Catalysis 2011 Volume 353( Issue 8) pp:1218-1222

Publication Date(Web):

DOI:10.1002/adsc.201000880

Abstract

Substituents create access to molecular diversity. Under basic conditions, 6-azabicyclo[3.2.1]oct-6-en-2-ones 3 and pyrrolizidines 4 are efficiently synthesized, respectively, in a single step from ethyl isocyanoacetate 2 and divinyl ketones 1 bearing an aryl or alkyl group at the 2-position. For comparison, only the corresponding pyrrolizidines 4′ can be obtained from divinyl ketones 1′ bearing a methoxycarbonyl group at the 2-position.

Polarity-Reversible Conjugate Addition Tuned by Remote Electronic Effects

Co-reporter:Yifei Li, Xianxiu Xu, Jing Tan, Peiqiu Liao, Jingping Zhang and Qun Liu

Organic Letters 2010 Volume 12(Issue 2) pp:244-247

Publication Date(Web):December 17, 2009

DOI:10.1021/ol902551m

A new concept, polarity-reversible conjugate addition, has been described, based on the findings that the polarity of a classical Michael acceptor can be reversed through remote electronic effects. In addition, the remote electronic effects are tunable, and both five- and six-membered nitrogen rings can be constructed starting from acyclic precursors having the same enone structure unit simply by varying a remote substituent in the molecules.

Tandem Michael addition/intramolecular isocyanide [3 + 2] cycloaddition: highly diastereoselective one pot synthesis of fused oxazolines

Co-reporter:Lingjuan Zhang, Xianxiu Xu, Jing Tan, Ling Pan, Wenming Xia and Qun Liu

Chemical Communications 2010 vol. 46(Issue 19) pp:3357-3359

Publication Date(Web):25 Mar 2010

DOI:10.1039/C001617A

A base-catalyzed tandem Michael addition/intramolecular isocyanide [3 + 2] cycloaddition of ethyl isocyanoacetate and Michael acceptors with tethered carbonyl groups is described. This reaction leads to the formation of fused oxazolines in a highly diastereoselective manner under very mild conditions.

Efficient synthesis of highly functionalized vinylogous thiol esters

Co-reporter:Jinglin Liu, Xianxiu Xu, Dongwei Li, Lei Zhang, Kun Zhang, Qun Liu

Tetrahedron Letters 2010 Volume 51(Issue 52) pp:6918-6920

Publication Date(Web):29 December 2010

DOI:10.1016/j.tetlet.2010.10.129

Tandem Double-Michael-Addition/Cyclization/Acyl Migration of 1,4-Dien-3-ones and Ethyl Isocyanoacetate: Stereoselective Synthesis of Pyrrolizidines

Co-reporter:Jing Tan, Dr.;Lingjuan Zhang;Yifei Li ;Qun Liu

Angewandte Chemie International Edition 2009 Volume 48( Issue 16) pp:2868-2872

Publication Date(Web):

DOI:10.1002/anie.200805703

Tandem Double-Michael-Addition/Cyclization/Acyl Migration of 1,4-Dien-3-ones and Ethyl Isocyanoacetate: Stereoselective Synthesis of Pyrrolizidines

Co-reporter:Jing Tan, Dr.;Lingjuan Zhang;Yifei Li ;Qun Liu