Yi-xia Jia

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Organization: Zhejiang University of Technology

Department: College of Chemical Engineering and Materials Science

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TOPICS

Organic Chemistry

Asymmetric Synthesis

Chemicals
References

Ir(I)-catalyzed enantioselective hydrogenolysis of 3-aryl-3-hydroxyisoindolin-1-ones

Co-reporter:Chen Ge, Ren-Xiao Liang, Ren-Rong Liu, Bin Xiang, Yi-Xia Jia

Tetrahedron Letters 2017 Volume 58(Issue 2) pp:142-144

Publication Date(Web):11 January 2017

DOI:10.1016/j.tetlet.2016.11.111

•Transition-metal-catalyzed asymmetric hydrogenolysis of hemiaminal is developed.•Molecular hydrogen is used as hydride source.•Chiral iridium complex is used for the first time in asymmetric hydrogenolysis.An enantioselective hydrogenolysis of 3-aryl-3-hydroxyisoindolin-1-ones under H2 has been developed by using Ir(I)/(R)-MeO-Biphep complex as a catalyst. Cyclic diaryl methylamides were obtained in moderate to excellent yields and up to 92% ee.

Spirooxindole synthesis via palladium-catalyzed dearomative reductive-Heck reaction

Co-reporter:Ren-Rong Liu;Yang Xu;Ren-Xiao Liang;Bin Xiang;Hu-Jun Xie;Jian-Rong Gao

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 13) pp:2711-2715

Publication Date(Web):2017/03/28

DOI:10.1039/C7OB00146K

Palladium-catalyzed intramolecular dearomative reductive-Heck reaction of C2-substituted indoles is developed, which provides access to structurally diverse 3,2′-spiropyrrolidine oxindoles. By changing the hydride source to AcONa base, direct C3-arylation products [2,3-b]quinolinones are achieved in good yields. The reaction of C2-substituted benzofuran is also realized, delivering the desired spiro-product.

Recent progress in transition-metal-catalyzed enantioselective indole functionalizations

Co-reporter:Jing-Biao Chen

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 17) pp:3550-3567

Publication Date(Web):2017/05/03

DOI:10.1039/C7OB00413C

Numerous efficient synthetic methods for enantioselective indole functionalizations have emerged in recent years. This review summarizes the major achievements in the transition-metal-catalyzed enantioselective indole functionalization reactions since 2010 and focuses on C–C bond formation processes, including alkylations, arylations, cycloaddition reactions, and other reactions. It intends to give a compendious overview of the significant progress achieved in this area.

Enantioselective Dearomative Difunctionalization of Indoles by Palladium-Catalyzed Heck/Sonogashira Sequence

Co-reporter:Dr. Ren-Rong Liu;Yong-Gang Wang;Ying-Long Li;Bing-Bing Huang;Dr. Ren-Xiao Liang; Dr. Yi-Xia Jia

Angewandte Chemie International Edition 2017 Volume 56(Issue 26) pp:7475-7478

Publication Date(Web):2017/06/19

DOI:10.1002/anie.201703833

AbstractPalladium-catalyzed enantioselective dearomative arylalkynylation of N-substituted indoles, through a Heck/Sonogashira sequence, was established using a new BINOL-based phosphoramidite as the chiral ligand. A wide range of 2,3-disubstituted indolines, bearing vicinal quaternary and tertiary stereocenters, were efficiently constructed in one step with excellent enantioselectivities (up to 97 % ee) and diastereoselectivities (>20:1).

Enantioselective alkynylation of N-sulfonyl α-ketiminoesters via a Friedel–Crafts alkylation strategy

Co-reporter:Ren-Rong Liu;Lei Zhu;Jiang-Ping Hu;Chuan-Jun Lu;Jian-Rong Gao;Yu Lan

Chemical Communications 2017 vol. 53(Issue 43) pp:5890-5893

Publication Date(Web):2017/05/30

DOI:10.1039/C7CC01015J

Enantioselective alkynylation of cyclic N-sulfonyl α-ketiminoesters with terminal alkynes was developed by using an Ni(ClO4)2/(R)-DTBM-Segphos complex as a catalyst. A range of propargylic amides bearing quaternary stereocenters were afforded in excellent enantioselectivities (up to 97% ee). Theoretical studies revealed that this reaction proceeded via a Friedel–Crafts-type reaction pathway.

Enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines: access to polysubstituted azetidines bearing quaternary stereocenters

Co-reporter:Ren-Rong Liu;Jiang-Ping Hu;Jian-Jun Hong;Chuan-Jun Lu;Jian-Rong Gao

Chemical Science (2010-Present) 2017 vol. 8(Issue 4) pp:2811-2815

Publication Date(Web):2017/03/28

DOI:10.1039/C6SC05450A

A Ni(ClO4)2-catalyzed enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines was developed, which regioselectively occurred at the proximal CC bonds of the N-allenamides. Broad substrate scope of N-allenamides and cyclic N-sulfonylketimines was observed. A range of fused polysubstituted azetidines bearing quaternary stereocenters were afforded in good yields and with excellent enantioselectivities (up to 99%).

Palladium/l-Proline-Catalyzed Enantioselective α-Arylative Desymmetrization of Cyclohexanones

Co-reporter:Ren-Rong Liu; Bao-Le Li; Jun Lu; Chong Shen; Jian-Rong Gao

Journal of the American Chemical Society 2016 Volume 138(Issue 16) pp:5198-5201

Publication Date(Web):April 14, 2016

DOI:10.1021/jacs.6b01214

A highly enantioselective palladium/l-proline-catalyzed α-arylative desymmetrization of cyclohexanones was developed. The new strategy for α-arylation reaction led to a series of optically active morphan derivatives bearing α-carbonyl tertiary stereocenters in good yields with excellent enantioselectivities (up to 99% ee).

Cu(I)-Catalyzed Enantioselective Friedel–Crafts Alkylation of Indoles with 2-Aryl-N-sulfonylaziridines as Alkylating Agents

Co-reporter:Chen Ge, Ren-Rong Liu, Jian-Rong Gao, and Yi-Xia Jia

Organic Letters 2016 Volume 18(Issue 13) pp:3122-3125

Publication Date(Web):June 16, 2016

DOI:10.1021/acs.orglett.6b01317

A highly enantioselective Friedel–Crafts alkylation of indoles with N-sulfonylaziridines as alkylating agents has been developed by utilizing the complex of Cu(CH3CN)4BF4/(S)-Segphos as a catalyst. A range of optically active tryptamine derivatives are obtained in good to excellent yields and enantioselectivities (up to >99% ee) via a kinetic resolution process.

Enantioselective Friedel–Crafts Alkylation Reactions of 3-Substituted Indoles with Electron-Deficient Alkenes

Co-reporter:Jian-Quan Weng, Ren-Jie Fan, Qiao-Man Deng, Ren-Rong Liu, Jian-Rong Gao, and Yi-Xia Jia

The Journal of Organic Chemistry 2016 Volume 81(Issue 7) pp:3023-3030

Publication Date(Web):March 9, 2016

DOI:10.1021/acs.joc.6b00123

Highly enantioselective Friedel–Crafts C2-alkylation reactions of 3-substituted indoles with α,β-unsaturated esters and nitroalkenes were developed using chiral Lewis acids as catalysts, which afforded chiral indole derivatives bearing C2-benzylic stereogenic centers in good to excellent yields (up to 99%) and enantioselectivities (up to 96% ee).

Lewis Acid Catalyzed Friedel–Crafts Alkylation of Alkenes with Trifluoropyruvates

Co-reporter:Bin Xiang, Teng-Fei Xu, Liang Wu, Ren-Rong Liu, Jian-Rong Gao, and Yi-Xia Jia

The Journal of Organic Chemistry 2016 Volume 81(Issue 9) pp:3929-3935

Publication Date(Web):March 30, 2016

DOI:10.1021/acs.joc.6b00358

A Friedel–Crafts alkylation reaction of styrenes with trifluoropyruvates has been developed, which delivered allylic alcohols in excellent yields (up to 98%) using the Ni(ClO4)2·6H2O/bipyridine complex as a catalyst. The asymmetric reaction was catalyzed by the chiral Cu(OTf)2/bisoxazoline complex to afford the corresponding chiral allylic alcohols bearing trifluoromethylated quaternary stereogenic centers in moderate enantioselectivities (up to 75% ee).

Enantioselective Arylative Dearomatization of Indoles via Pd-Catalyzed Intramolecular Reductive Heck Reactions

Co-reporter:Chong Shen; Ren-Rong Liu; Ren-Jie Fan; Ying-Long Li; Teng-Fei Xu; Jian-Rong Gao

Journal of the American Chemical Society 2015 Volume 137(Issue 15) pp:4936-4939

Publication Date(Web):April 7, 2015

DOI:10.1021/jacs.5b01705

A highly enantioselective intramolecular arylative dearomatization of indoles via palladium-catalyzed reductive Heck reactions was developed. The new strategy led to a series of optically active indolines bearing C2-quaternary stereocenters in modest to good yields with excellent enantioselectivities (up to 99% ee).

Nickel-Catalyzed Enantioselective Addition of Styrenes to Cyclic N-Sulfonyl α-Ketiminoesters

Co-reporter:Ren-Rong Liu, Dan-Jie Wang, Liang Wu, Bin Xiang, Guo-Qi Zhang, Jian-Rong Gao, and Yi-Xia Jia

ACS Catalysis 2015 Volume 5(Issue 11) pp:6524

Publication Date(Web):October 2, 2015

DOI:10.1021/acscatal.5b01793

Enantioselective addition of styrenes to cyclic N-sulfonyl α-ketiminoesters was developed using the complex of Ni(ClO4)2 with chiral phosphine complex as a catalyst. A range of chiral benzofused 5-membered sultams bearing alkenylated or allylated α-tetrasubstituted amino ester framework were afforded in excellent enantioselectivities (up to 99% ee) as potential biologically active compounds for drug research.Keywords: asymmetric catalysis; nickel; quaternary stereocenter; styrene; sultam

Indolizine Synthesis via Oxidative Cross-Coupling/Cyclization of Alkenes and 2-(Pyridin-2-yl)acetate Derivatives

Co-reporter:Ren-Rong Liu, Jian-Jun Hong, Chuan-Jun Lu, Meng Xu, Jian-Rong Gao, and Yi-Xia Jia

Organic Letters 2015 Volume 17(Issue 12) pp:3050-3053

Publication Date(Web):June 11, 2015

DOI:10.1021/acs.orglett.5b01334

A novel copper/I2-mediated oxidative cross-coupling/cyclization of 2-(pyridin-2-yl)acetate derivatives and simple olefins is developed, which provides a straightforward and efficient access to structural diversely indolizines. A series of 1,3-di- and 1,2,3-trisubstituted indolizines are easily synthesized in modest to excellent yields.

Enantioselective Construction of Cyclic Indolyl -Amino Esters via a FriedelCrafts Alkylation Reaction

Co-reporter:Liang Wu;Ren-Rong Liu;Guoqi Zhang;Dan-Jie Wang;Hao Wu;Jianrong Gao

Advanced Synthesis & Catalysis 2015 Volume 357( Issue 4) pp:709-713

Publication Date(Web):

DOI:10.1002/adsc.201400987

Au-catalyzed ring-opening reactions of 2-(1-alkynyl-cyclopropyl)pyridines with nucleophiles

Co-reporter:Ren-Rong Liu, Shi-Chun Ye, Chuan-Jun Lu, Bin Xiang, Jianrong Gao and Yi-Xia Jia

Organic & Biomolecular Chemistry 2015 vol. 13(Issue 17) pp:4855-4858

Publication Date(Web):23 Mar 2015

DOI:10.1039/C5OB00523J

A novel method for the C–C bond cleavage of cyclopropanes was developed by gold-catalyzed cycloisomerization of 2-(1-alkynyl-cyclopropyl)pyridine with nucleophiles, which provides efficient access to structurally diverse indolizines under mild conditions. A series of N-, C- and O-based nucleophiles were involved in this reaction to afford the corresponding indolizines in modest to excellent yields.

CuSO4-mediated decarboxylative C–N cross-coupling of aromatic carboxylic acids with amides and anilines

Co-reporter:Wei-Jian Sheng, Qing Ye, Wu-Bin Yu, Ren-Rong Liu, Meng Xu, Jian-Rong Gao, Yi-Xia Jia

Tetrahedron Letters 2015 Volume 56(Issue 4) pp:599-601

Publication Date(Web):21 January 2015

DOI:10.1016/j.tetlet.2014.12.085

CuSO4-mediated decarboxylative C–N cross-coupling of aromatic carboxylic acid with amide has been developed, leading to N-arylamides in modest to excellent yields. Anilines bearing electron-withdrawing substituents could also couple efficiently with aromatic carboxylic acids to give diarylamines in good to excellent yields.

Dual Catalysis for the Redox Annulation of Nitroalkynes with Indoles: Enantioselective Construction of Indolin-3-ones Bearing Quaternary Stereocenters

Co-reporter:Dr. Ren-Rong Liu;Shi-Chun Ye;Dr. Chuan-Jun Lu;Dr. Gui-Lin Zhuang;Dr. Jian-Rong Gao ;Dr. Yi-Xia Jia

Angewandte Chemie 2015 Volume 127( Issue 38) pp:11357-11360

Publication Date(Web):

DOI:10.1002/ange.201504697

Abstract

The enantioselective redox annulation of nitroalkynes with indoles is enabled by gold/chiral phosphoric acid dual catalysis. A range of indolin-3-one derivatives bearing quaternary stereocenters at the C2 position were afforded in good yields and excellent enantioselectivities (up to 96 % ee) from readily available starting materials.

Dual Catalysis for the Redox Annulation of Nitroalkynes with Indoles: Enantioselective Construction of Indolin-3-ones Bearing Quaternary Stereocenters

Co-reporter:Dr. Ren-Rong Liu;Shi-Chun Ye;Dr. Chuan-Jun Lu;Dr. Gui-Lin Zhuang;Dr. Jian-Rong Gao ;Dr. Yi-Xia Jia

Angewandte Chemie International Edition 2015 Volume 54( Issue 38) pp:11205-11208

Publication Date(Web):

DOI:10.1002/anie.201504697

Abstract

Palladium-Catalyzed Three-Component Cascade Reaction: Facial Access to Densely Functionalized Indolizines

Co-reporter:Ren-Rong Liu;Chuan-Jun Lu;Ming-Di Zhang;Jian-Rong Gao ;Dr. Yi-Xia Jia

Chemistry - A European Journal 2015 Volume 21( Issue 19) pp:7057-7060

Publication Date(Web):

DOI:10.1002/chem.201500569

Abstract

A palladium-catalyzed three-component cascade reaction of 2-(2-enynyl)pyridines with nucleophiles and allyl halides has been developed, enabling the synthesis of densely functionalized indolizines in moderate to good yields. The newly developed methodology offers several practical advantages, including operational simplicity, ready availability of starting materials, and mild reaction conditions.

Asymmetric Friedel–Crafts Alkylation of α-Substituted β-Nitroacrylates: Access to β2,2-Amino Acids Bearing Indolic All-Carbon Quaternary Stereocenters

Co-reporter:Jian-Quan Weng, Qiao-Man Deng, Liang Wu, Kai Xu, Hao Wu, Ren-Rong Liu, Jian-Rong Gao, and Yi-Xia Jia

Organic Letters 2014 Volume 16(Issue 3) pp:776-779

Publication Date(Web):January 10, 2014

DOI:10.1021/ol403480v

A highly enantioselective Friedel–Crafts alkylation reaction of indoles with acyclic α-substituted β-nitroacrylates is developed under the catalysis of Ni(ClO4)2–bisoxazoline complex at 1 mol % catalyst loading, affording chiral indolic β-nitroesters bearing all-carbon quaternary stereocenters in excellent yields and ees of up to 97%. Transformation of one of the products to β2,2-amino ester and tetrahydro-β-carboline through nitro reduction and sequential Pictet–Spengler cyclization was exemplified.

Nickel-catalyzed intramolecular addition of vinyl or aryl bromides to ketoamides

Co-reporter:Jun-Qing He, Cheng Chen, Wu-Bin Yu, Ren-Rong Liu, Meng Xu, Yu-Jin Li, Jian-Rong Gao, Yi-Xia Jia

Tetrahedron Letters 2014 Volume 55(Issue 17) pp:2805-2808

Publication Date(Web):23 April 2014

DOI:10.1016/j.tetlet.2014.03.069

A nickel-catalyzed intramolecular addition of vinyl or aryl bromides to ketoamides has been developed. The reactions proceeded efficiently with Ni(bpy)Br2 as a catalyst and zinc powder as reducing agent, affording 3-hydroxypyrrolidinones, 3-hydroxyoxindoles, and dihydroquinolinones as important heterocyclic compounds in good to excellent yields.

Highly Enantioselective Construction of Trifluoromethylated All-Carbon Quaternary Stereocenters via Nickel-Catalyzed Friedel–Crafts Alkylation Reaction

Co-reporter:Jian-Rong Gao ; Hao Wu ; Bin Xiang ; Wu-Bin Yu ; Liang Han

Journal of the American Chemical Society 2013 Volume 135(Issue 8) pp:2983-2986

Publication Date(Web):February 14, 2013

DOI:10.1021/ja400650m

A highly enantioselective Friedel–Crafts alkylation reaction of indoles with β-CF3-β-disubstituted nitroalkenes was achieved using a Ni(ClO4)2–bisoxazoline complex as a catalyst, which afforded indole-bearing chiral compounds with trifluoromethylated all-carbon quaternary stereocenters in good yields with excellent enantioselectivities (up to 97% ee). The transformation of one of the products into first a trifluoromethylated tryptamine and then a trifluoromethylated tetrahydro-β-carboline by sequential nitro reduction and Pictet–Spengler cyclization were realized with complete preservation of enantiopurity.

Chiral phosphoric acid catalyzed asymmetric hydrogenolysis of racemic 3-aryl-3-hydroxyisoindolin-1-ones

Co-reporter:Jian-Qing Zhou, Wei-Jian Sheng, Jian-Hong Jia, Qing Ye, Jian-Rong Gao, Yi-Xia Jia

Tetrahedron Letters 2013 Volume 54(Issue 24) pp:3082-3084

Publication Date(Web):12 June 2013

DOI:10.1016/j.tetlet.2013.03.138

The enantioselective hydrogenolysis of racemic 3-aryl-3-hydroxyisoindolin-1-ones catalyzed by BINOL-derived chiral phosphoric acid with benzothiazoline as the hydride source is described. The corresponding cyclic diaryl methylamines are obtained in good to excellent yields and up to 91% enantioselectivities.

Nickel-Catalyzed Intramolecular Nucleophilic Addition of Aryl or Vinyl Chlorides to -Ketoamides Through CCl Bond Activation

Co-reporter:Jin-Xiu Hu;Hao Wu;Dr. Chuan-Ying Li;Wei-Jian Sheng;Dr. Yi-Xia Jia;Dr. Jian-Rong Gao

Chemistry - A European Journal 2011 Volume 17( Issue 19) pp:5234-5237

Publication Date(Web):

DOI:10.1002/chem.201100256

Au-catalyzed ring-opening reactions of 2-(1-alkynyl-cyclopropyl)pyridines with nucleophiles

Co-reporter:Ren-Rong Liu, Shi-Chun Ye, Chuan-Jun Lu, Bin Xiang, Jianrong Gao and Yi-Xia Jia

Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 17) pp:NaN4858-4858

Publication Date(Web):2015/03/23

DOI:10.1039/C5OB00523J

Enantioselective alkynylation of N-sulfonyl α-ketiminoesters via a Friedel–Crafts alkylation strategy

Co-reporter:Ren-Rong Liu, Lei Zhu, Jiang-Ping Hu, Chuan-Jun Lu, Jian-Rong Gao, Yu Lan and Yi-Xia Jia

Chemical Communications 2017 - vol. 53(Issue 43) pp:NaN5893-5893

Publication Date(Web):2017/05/10

DOI:10.1039/C7CC01015J

Spirooxindole synthesis via palladium-catalyzed dearomative reductive-Heck reaction

Co-reporter:Ren-Rong Liu, Yang Xu, Ren-Xiao Liang, Bin Xiang, Hu-Jun Xie, Jian-Rong Gao and Yi-Xia Jia

Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 13) pp:NaN2715-2715

Publication Date(Web):2017/02/27

DOI:10.1039/C7OB00146K

Palladium-catalyzed dearomative arylalkynylation of indoles

Co-reporter:Ren-Rong Liu, Teng-Fei Xu, Yong-Gang Wang, Bin Xiang, Jian-Rong Gao and Yi-Xia Jia

Chemical Communications 2016 - vol. 52(Issue 94) pp:NaN13667-13667

Publication Date(Web):2016/09/29

DOI:10.1039/C6CC06262H

A palladium-catalyzed indole dearomative bisfunctionalization via a domino arylation/alkynylation sequence has been developed, which provides a reliable approach to a series of structurally diverse tetracyclic indolines bearing vicinal tertiary and quaternary stereocenters in moderate to good yields and excellent diastereoselectivities.

Enantioselective Friedel–Crafts reaction of 4,7-dihydroindoles with β-CF3-β-disubstituted nitroalkenes

Co-reporter:Hao Wu, Ren-Rong Liu, Chong Shen, Ming-Di Zhang, Jianrong Gao and Yi-Xia Jia

Inorganic Chemistry Frontiers 2015 - vol. 2(Issue 2) pp:NaN126-126

Publication Date(Web):2014/12/16

DOI:10.1039/C4QO00265B

Using a Ni(ClO4)2–bisoxazoline complex as a catalyst, Friedel–Crafts alkylations of 4,7-dihydroindoles with β-CF3-β-disubstituted nitroalkenes were carried out with high enantioselectivities (up to 91%) to give alkylated dihydroindoles bearing trifluoromethylated all-carbon quaternary stereocenters in good yields. The corresponding chiral C2 alkylated indoles were obtained with complete preservation of enantiomeric purity by oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).

Enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines: access to polysubstituted azetidines bearing quaternary stereocenters

Co-reporter:Ren-Rong Liu, Jiang-Ping Hu, Jian-Jun Hong, Chuan-Jun Lu, Jian-Rong Gao and Yi-Xia Jia

Chemical Science (2010-Present) 2017 - vol. 8(Issue 4) pp:NaN2815-2815

Publication Date(Web):2017/01/19

DOI:10.1039/C6SC05450A

Indolizine synthesis via Cu-catalyzed cyclization of 2-(2-enynyl)pyridines with nucleophiles

Co-reporter:Ren-Rong Liu, Zheng-Yi Cai, Chuan-Jun Lu, Shi-Chun Ye, Bin Xiang, Jianrong Gao and Yi-Xia Jia

Inorganic Chemistry Frontiers 2015 - vol. 2(Issue 3) pp:NaN230-230

Publication Date(Web):2015/01/14

DOI:10.1039/C4QO00336E

Efficient and atom-economical access to indolizines has been developed by a Cu-catalyzed cyclization of 2-(2-enynyl)pyridines with various nucleophiles through simultaneous formation of a C–N bond and a remote carbon–nucleophile bond. 1,3-Dicarbonyl compounds, indoles, amides, alcohol, and even water, were used as nucleophiles in this reaction. Good to excellent yields of the corresponding indolizines were obtained under mild reaction conditions.

Recent progress in transition-metal-catalyzed enantioselective indole functionalizations

Co-reporter:Jing-Biao Chen and Yi-Xia Jia

Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 17) pp:NaN3567-3567

Publication Date(Web):2017/03/23

DOI:10.1039/C7OB00413C