Xiyan Lu

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Organization: Shanghai Institute of Organic Chemistry

Department: State Key Laboratory of Organometallic Chemistry

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Organic Chemistry

allene

Chemicals
References

Atom-Economic Synthesis of Pentaleno[2,1-b]indoles via Tandem Cyclization of Alkynones Initiated by Aminopalladation

Co-reporter:Junjie Chen, Xiuling Han, and Xiyan Lu

The Journal of Organic Chemistry 2017 Volume 82(Issue 4) pp:

Publication Date(Web):January 14, 2017

DOI:10.1021/acs.joc.6b02817

An atom-economic Pd(OAc)2-catalyzed tandem cyclization of alkynones to synthesize pentaleno[2,1-b]indoles was developed efficiently. In the formed tetracyclic indole framework, two neighboring stereocenters, one being all-carbon quaternary, are being constructed in a single process with excellent diastereoselectivity. This reaction was initiated by aminopalladation of alkynes and quenched by addition to the intramolecular carbonyl groups.

Enantioselective Synthesis of Tetrahydropyrano[3,4-b]indoles: Palladium(II)-Catalyzed Aminopalladation/1,4-Addition Sequence

Co-reporter:Junjie Chen;Dr. Xiuling Han; Xiyan Lu

Angewandte Chemie International Edition 2017 Volume 56(Issue 46) pp:14698-14701

Publication Date(Web):2017/11/13

DOI:10.1002/anie.201708900

AbstractA novel palladium(II)-catalyzed cyclization of aniline-tethered alkynyl cyclohexadienones is reported. This reaction offers an atom-economical and redox-neutral access to various cyclohexenone-fused tetrahydropyrano[3,4-b]indoles with high yield and excellent enantioselectivity. Remarkably, this work represents the first example on a transition-metal-catalyzed asymmetric intramolecular aminopalladation/1,4 addition sequence.

Synthesis of Indole-Substituted Indanones via Palladium(II)-Catalyzed Tandem Reaction of ortho-Electron-Deficient Alkynyl-Substituted Aryl Aldehydes with Indoles

Co-reporter:Jianbo Zhang, Xiuling Han, and Xiyan Lu

Organic Letters 2016 Volume 18(Issue 12) pp:2898-2901

Publication Date(Web):May 26, 2016

DOI:10.1021/acs.orglett.6b01240

A Pd(OAc)2-catalyzed cyclization reaction of ortho-electron-deficient alkynyl-substituted aryl aldehydes with indoles was accomplished, providing an efficient and economical way to synthesize indole-substituted indanones. The electron-withdrawing group attached to the alkyne and the nucleophilic indole play important roles in the formation of the indanone ring.

Regiocontrolled Coupling of Aromatic and Vinylic Amides with α-Allenols To Form γ-Lactams via Rhodium(III)-Catalyzed C–H Activation

Co-reporter:Zhi Zhou, Guixia Liu, and Xiyan Lu

Organic Letters 2016 Volume 18(Issue 21) pp:5668-5671

Publication Date(Web):October 24, 2016

DOI:10.1021/acs.orglett.6b02903

A mild, regiocontrolled coupling of aromatic and vinylic amides with α-allenols to form γ-lactams via rhodium(III)-catalyzed C–H activation has been demonstrated. This [4 + 1] annulation reaction provides an efficient method for the synthesis of isoindolinones and 1,5-dihydro-pyrrol-2-ones bearing a tetrasubstituted carbon atom α to the nitrogen atom with good functional group tolerance. The hydroxyl group in the allene substrate is essential in controlling the chemo- and regioselectivity of the reaction probably by coordination interaction with the rhodium catalyst.

Synthesis of Cyclohexane-Fused Isocoumarins via Cationic Palladium(II)-Catalyzed Cascade Cyclization Reaction of Alkyne-Tethered Carbonyl Compounds Initiated by Intramolecular Oxypalladation of Ester-Substituted Aryl Alkynes

Co-reporter:Jianbo Zhang, Xiuling Han, and Xiyan Lu

The Journal of Organic Chemistry 2016 Volume 81(Issue 8) pp:3423-3429

Publication Date(Web):March 21, 2016

DOI:10.1021/acs.joc.6b00128

A cationic Pd(II)-catalyzed cascade cyclization reaction of alkyne-tethered carbonyl compounds was developed. This reaction is initiated by intramolecular oxypalladation of alkynes with an ester group followed by 1,2-addition of the formed C–Pd(II) bond to the carbonyl group, providing a highly efficient method for the synthesis of cyclohexane-fused isocoumarins.

Cationic Pd(II)-Catalyzed Cyclization of N-Tosyl-aniline Tethered Allenyl Aldehydes with Arylboronic Acids: Diastereo- and Enantioselective Synthesis of Tetrahydroquinoline Derivatives

Co-reporter:Xiaojuan Zhang, Xiuling Han, and Xiyan Lu

Organic Letters 2015 Volume 17(Issue 15) pp:3910-3913

Publication Date(Web):July 24, 2015

DOI:10.1021/acs.orglett.5b01894

An efficient cyclization of N-tosyl-aniline tethered allenyl aldehydes and arylboronic acids catalyzed by cationic palladium complex is developed. This annulation reaction provides a convenient process for the synthesis of 3,4-cis-1,2,3,4-tetrahydroquinoline derivatives in high yields with excellent diastereoselectivity and enantioselectivity.

Cascade Synthesis of 3-Alkylidene Dihydrobenzofuran Derivatives via Rhodium(III)-Catalyzed Redox-Neutral C–H Functionalization/Cyclization

Co-reporter:Zhi Zhou, Guixia Liu, Yan Chen, and Xiyan Lu

Organic Letters 2015 Volume 17(Issue 23) pp:5874-5877

Publication Date(Web):November 16, 2015

DOI:10.1021/acs.orglett.5b03060

An efficient rhodium(III)-catalyzed coupling reaction of N-phenoxyacetamides with propargyl carbonates to yield 3-alkylidene dihydrobenzofuran derivatives via C–H functionalization/cascade cyclization has been developed. This transformation represents a redox-neutral process and features the formation of three new bonds under mild conditions.

Efficient Synthesis of Heterocyle-Fused β-Naphthylamines via Intramolecular Addition to a Cyano Group Initiated by Nucleopalladation of Alkynes

Co-reporter:Guoqin Xia, Xiuling Han, and Xiyan Lu

Organic Letters 2014 Volume 16(Issue 23) pp:6184-6187

Publication Date(Web):November 17, 2014

DOI:10.1021/ol5031074

A palladium(II)-catalyzed efficient synthesis of heterocycle-fused β-naphthylamines was accomplished via nucleophilic addition of a carbon–palladium bond to the intramolecular cyano group initiated by nucleopalladation (oxypalladation or aminopalladation) of alkynes.

Pd(II)-Catalyzed One-Step Construction of Cycloalkane-Fused Indoles and Its Application in Formal Synthesis of (±)-Aspidospermidine

Co-reporter:Guoqin Xia, Xiuling Han, and Xiyan Lu

Organic Letters 2014 Volume 16(Issue 7) pp:2058-2061

Publication Date(Web):March 21, 2014

DOI:10.1021/ol500662f

A highly efficient, redox-free Pd(II)-catalyzed tandem cyclization reaction initiated by intramolecular aminopalladation of alkynes followed by nucleophilic addition to nitriles is developed. This method provides a versatile approach for the synthesis of six- to eight-membered ring-fused indoles in one step and has also shown advantages in the formal synthesis of (±)-aspidospermidine.

Palladium(II)-catalyzed oxidative annulation of alkenylindoles with alkynes initiated by C–H activation

Co-reporter:Tao Su, Xiuling Han, Xiyan Lu

Tetrahedron Letters 2014 Volume 55(Issue 1) pp:27-30

Publication Date(Web):1 January 2014

DOI:10.1016/j.tetlet.2013.10.079

A palladium(II)-catalyzed annulation of alkenylindoles with diarylethynes initiated by C–H bond activation was developed. This method provided a convenient way for the synthesis of dihydrocyclopenta[b]indoles by enyne cyclization initiated by C–H bond activation.

Cationic Pd(II)-Catalyzed Reductive Cyclization of Alkyne-Tethered Ketones or Aldehydes Using Ethanol as Hydrogen Source

Co-reporter:Kun Shen, Xiuling Han, and Xiyan Lu

Organic Letters 2013 Volume 15(Issue 7) pp:1732-1735

Publication Date(Web):March 21, 2013

DOI:10.1021/ol400531a

A cationic Pd(II)-catalyzed reductive cyclization of alkyne-tethered ketones or aldehydes using ethanol as hydrogen source under mild conditions was developed. The reaction is an environmentally benign synthetic method and proceeds efficiently to give useful N-heterocycles or carbocycles bearing an exocyclic double bond and a hydroxyl group in high yield.

Palladium(II)-catalyzed tandem annulation reaction of o-alkynylbenzoates with methyl vinyl ketone for the synthesis of isocoumarins

Co-reporter:Huan Wang, Xiuling Han, Xiyan Lu

Tetrahedron 2013 69(40) pp: 8626-8631

Publication Date(Web):

DOI:10.1016/j.tet.2013.07.057

Cationic Pd(II)-Catalyzed Highly Enantioselective Arylative Cyclization of Alkyne-Tethered Enals or Enones Initiated by Carbopalladation of Alkynes with Arylboronic Acids

Co-reporter:Kun Shen, Xiuling Han, and Xiyan Lu

Organic Letters 2012 Volume 14(Issue 7) pp:1756-1759

Publication Date(Web):March 26, 2012

DOI:10.1021/ol3003546

Cationic Pd(II)-catalyzed enantioselective arylative cyclization of alkyne-tethered enals or enones initiated by carbopalladation of alkynes was developed without the necessity of a redox system.

Efficient Synthesis of 9-Tosylaminofluorene Derivatives by Boron Trifluoride Etherate-Catalyzed Aza-FriedelCrafts Reaction of in situ Generated N-Tosylbenzaldimines

Co-reporter:Xufen Yu

Advanced Synthesis & Catalysis 2011 Volume 353( Issue 4) pp:569-574

Publication Date(Web):

DOI:10.1002/adsc.201000732

Abstract

An efficient and expeditious boron trifluoride etherate (BF₃⋅Et₂O) catalyzed one-pot reaction for the synthesis of N-tosyl-9-aminofluorenes and anthracene derivatives from in situ generated N-tosylbenzaldimines via an aza-Friedal–Crafts reaction has been developed. The catalytic reaction shows high substrate tolerance with excellent yields.

Cationic Palladium Complex-Catalyzed Diastereoselective Tandem Annulation of 2-Iminoarylboronic Acids with Substituted Alkynes: Enantioselective Synthesis of Aminoindene Derivatives by Double Asymmetric Induction

Co-reporter:Xufen Yu

Advanced Synthesis & Catalysis 2011 Volume 353( Issue 14-15) pp:2805-2813

Publication Date(Web):

DOI:10.1002/adsc.201100363

Abstract

The tandem annulation reaction of 2-iminoarylboronic acids and alkynes was developed for the synthesis of aminoindene derivatives catalyzed by cationic palladium complex. In addition, an enantioselective synthesis of aminoindene derivatives from the reaction of substituted (S)-2-(N-tert-butanesulfinylimino)arylboronic acids with a variety of alkynes catalyzed by chiral cationic palladium complex was also achieved by the double asymmetric induction.

Pd(OAc)2-Catalyzed Tandem Reactions for the Synthesis of Indol-3-yl Substituted 1H-Isochromenes and 1,2-Dihydroisoquinolines

Co-reporter:Huan Wang;Xiuling Han

Chinese Journal of Chemistry 2011 Volume 29( Issue 12) pp:2611-2618

Publication Date(Web):

DOI:10.1002/cjoc.201100390

Abstract

A Pd(II) catalyzed tandem reaction of o-alkynylbenzaldehydes or o-alkynylbenzaldimines with substituted indoles initiated by the intermolecular addition of indoles to the carbonyl or imine group followed by the nucleopalladation of an intramolecular alkyne and quenching the carbon-palladium bond by protonolysis to regenerate the Pd(II) species was developed. The reaction can be carried out under mild conditions without the necessity of a redox system.

Synthesis of indoles via palladium-catalyzed C–H activation of N-aryl amides followed by coupling with alkynes

Co-reporter:Feng Zhou, Xiuling Han, Xiyan Lu

Tetrahedron Letters 2011 Volume 52(Issue 36) pp:4681-4685

Publication Date(Web):7 September 2011

DOI:10.1016/j.tetlet.2011.07.009

A convenient and efficient method for the construction of indole skeleton was developed via Pd-catalyzed C–H activation of N-aryl amides and subsequent coupling with alkynes. Both stoichiometric and catalytic versions have been successfully achieved.

Facile Cu(OTf)2-catalyzed preparation of 9-tosylaminofluorene derivatives from o-arylated N-tosylbenzaldimines

Co-reporter:Xufen Yu, Xiyan Lu

Tetrahedron Letters 2011 Volume 52(Issue 17) pp:2076-2079

Publication Date(Web):27 April 2011

DOI:10.1016/j.tetlet.2010.10.110

The 9-tosylaminofluorene derivatives were synthesized conveniently by Cu(OTf)2-catalyzed aza-Friedel–Crafts reaction of o-arylated N-tosylbenzaldimines in high yields. This is an efficient, atom-economic, and green method.

Cationic Palladium-Catalyzed [5 + 2] Annulation of 2-Acylmethoxyarylboronic Acids and Allenoates: Synthesis of 1-Benzoxepine Derivatives

Co-reporter:Xufen Yu and Xiyan Lu

The Journal of Organic Chemistry 2011 Volume 76(Issue 15) pp:6350-6355

Publication Date(Web):July 11, 2011

DOI:10.1021/jo200672w

The 1-benzoxepine derivatives were synthesized conveniently by cationic palladium-catalyzed [5 + 2] annulation reaction of 2-acylmethoxyarylboronic acids with allenoates in high yields. This annulation involves the intramolecular nucleophilic addition to ketones without the formation of π-allylpalladium species.

Control of Chemoselectivity by Counteranions of Cationic Palladium Complexes: A Convenient Enantioselective Synthesis of Dihydrocoumarins

Co-reporter:Xiuling Han and Xiyan Lu

Organic Letters 2010 Volume 12(Issue 1) pp:108-111

Publication Date(Web):December 7, 2009

DOI:10.1021/ol902538n

High chemoselectivity for the synthesis of two kinds of substituted coumarins controlled by the counteranions of the cationic palladium catalysts is described. The asymmetric version of the reaction for the synthesis of 3-alkylidene dihydrocoumarins is realized with high enantioselectivity.

Cationic Pd(II)-Catalyzed Tandem Reaction of 2-Arylethynylanilines and Aldehydes: An Efficient Synthesis of Substituted 3-Hydroxymethyl Indoles

Co-reporter:Xiuling Han and Xiyan Lu

Organic Letters 2010 Volume 12(Issue 15) pp:3336-3339

Publication Date(Web):July 12, 2010

DOI:10.1021/ol1011086

An efficient cationic palladium(II)-catalyzed synthesis of substituted 3-hydroxymethylindoles from readily accessible starting materials is developed. This tandem reaction involves an intramolecular aminopalladation of an alkyne and an addition to the carbonyl group to quench the carbon−palladium bond to complete the catalytic cycle without the necessity of a redox system.

Cationic Pd(II)/Bipyridine-Catalyzed Conjugate Addition of Arylboronic Acids to β,β-Disubstituted Enones: Construction of Quaternary Carbon Centers

Co-reporter:Shaohui Lin and Xiyan Lu

Organic Letters 2010 Volume 12(Issue 11) pp:2536-2539

Publication Date(Web):May 7, 2010

DOI:10.1021/ol100767u

Cationic Pd(II)-catalyzed addition of arylboronic acids to β,β-disubstituted enones in high yields was developed. This method provided an efficient method for the construction of quaternary carbon centers, and only 0.5 mol % of Pd(II) catalyst was needed.

Pd(II)-catalyzed annulation of N-benzyl-N-aroylmethyl-2-alkynamides with arylboronic acids: an efficient synthesis of highly substituted α-alkylidene-β-hydroxy-γ-lactams

Co-reporter:Huan Wang, Xiuling Han, Xiyan Lu

Tetrahedron 2010 66(47) pp: 9129-9134

Publication Date(Web):

DOI:10.1016/j.tet.2010.09.090

Novel Palladium-Catalyzed Acyloxylation/Cyclization of 2-(3′-Alkenyl)indoles

Co-reporter:Xiuling Han and Xiyan Lu

Organic Letters 2009 Volume 11(Issue 11) pp:2381-2384

Publication Date(Web):May 6, 2009

DOI:10.1021/ol9007348

A new and mild palladium(II)-catalyzed reaction for the intramolecular acyloxylation/cyclization of 2-(3′-alkenyl)indoles was developed. The newly formed cycles involve oxygen-containing functionalized groups, which might be transferred further to provide other indole derivatives.

Phosphine-Catalyzed [4 + 3] Annulation for the Synthesis of Highly Functionalized Bicyclo[3.2.2]nonadienes

Co-reporter:Suqing Zheng and Xiyan Lu

Organic Letters 2009 Volume 11(Issue 17) pp:3978-3981

Publication Date(Web):August 11, 2009

DOI:10.1021/ol901618h

A phosphine-catalyzed [4 + 3] annulation of modified allylic carbonates with methyl coumalate was developed. This strategy offered a powerful method for the construction of bicyclo[3.2.2]nonadiene skeleton with high stereoselectivity.

Cationic Palladium Complex Catalyzed Diastereo- and Enantioselective Tandem Annulation of 2-Formylarylboronic Acids with Allenoates

Co-reporter:Xufen Yu and Xiyan Lu

Organic Letters 2009 Volume 11(Issue 19) pp:4366-4369

Publication Date(Web):August 31, 2009

DOI:10.1021/ol901714d

Cationic palladium complex [(dppp)Pd(H2O)2]2+(BF4−)2 catalyzed tandem annulation reactions of 2-formylarylboronic acids and allenoates produce the indenol derivatives diastereo- and enantioselectively in a highly efficient way.

Cupric Halide-Mediated Intramolecular Halocyclization of N-Electron-Withdrawing Group-Substituted 2-Alkynylanilines for the Synthesis of 3-Haloindoles

Co-reporter:Zengming Shen

Advanced Synthesis & Catalysis 2009 Volume 351( Issue 18) pp:3107-3112

Publication Date(Web):

DOI:10.1002/adsc.200900609

Abstract

A convenient and efficient method for the synthesis of 3-haloindoles has been developed. Both 3-chloro- and 3-bromoindole derivatives can be obtained in high yields by the reaction of N-electron-withdrawing group-substituted 2-alkynylanilines with cupric halide in dimethyl sulfoxide (DMSO) within a short period of time. Investigation of the reaction mechanism reveals that two equivalents of cupric halide are necessary.

Palladium(II)/2,2′-bipyridine-catalyzed addition of arylboronic acids to N-tosyl-arylaldimines

Co-reporter:Huixiong Dai, Xiyan Lu

Tetrahedron Letters 2009 50(26) pp: 3478-3481

Publication Date(Web):

DOI:10.1016/j.tetlet.2009.03.005

Phosphine-catalyzed [3+3] annulation reaction of modified tert-butyl allylic carbonates and substituted alkylidenemalononitriles

Co-reporter:Suqing Zheng, Xiyan Lu

Tetrahedron Letters 2009 50(31) pp: 4532-4535

Publication Date(Web):

DOI:10.1016/j.tetlet.2009.05.085

Palladium(II)-Catalyzed One-Pot Enantioselective Synthesis of Arylglycine Derivatives from Ethyl Glyoxylate, p-Toluenesulfonyl Isocyanate and Arylboronic Acids

Co-reporter:Huixiong Dai;Miao Yang

Advanced Synthesis & Catalysis 2008 Volume 350( Issue 2) pp:249-253

Publication Date(Web):

DOI:10.1002/adsc.200700362

Abstract

A palladium(II)-catalyzed, one-pot enantioselective synthesis of arylglycine derivatives from ethyl glyoxylate, p-toluenesulfonyl isocyanate and arylboronic acids giving moderate to good yields and enantioselectivity has been developed. This reaction provides a convenient and efficient method for the synthesis of arylglycines.

Cationic Palladium-Catalyzed [5+2] Annulation: Synthesis of 1-Benzoxepines from 2-Aroylmethoxyarylboronic Acids

Co-reporter:Guixia Liu

Advanced Synthesis & Catalysis 2007 Volume 349(Issue 14-15) pp:

Publication Date(Web):4 OCT 2007

DOI:10.1002/adsc.200700369

The synthesis of 1-benzoxepines from 2-aroylmethoxyarylboronic acids and alkynes in the presence of a catalytic amount of [Pd(dppp)(H₂O)₂]²⁺(TfO⁻)₂ was developed. This [5+2] annulation involves the intramolecular nucleophilic addition of a vinylpalladium species to ketones.

Cationic Pd(II)-catalyzed arylative cyclization of N-(2-formylaryl)alkynamides: An efficient route to 2-quinolinones

Co-reporter:Xiaojuan Zhang, Xiuling Han, Junjie Chen, Xiyan Lu

Tetrahedron (23 March 2017) Volume 73(Issue 12) pp:

Publication Date(Web):23 March 2017

DOI:10.1016/j.tet.2017.01.053

A cationic palladium complex catalyzed arylative cyclization reaction of N-(2-formylaryl)alkynamides with arylboronic acids was developed. This new process provides an efficient way for the synthesis of functionalized 2-quinolinones in good to excellent yields under mild conditions. Some control experiments were conducted to explain the possible mechanism for the formation of the products.