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Artículos de revistas sobre el tema "Aza-Wacker"

Autor: Grafiati
Publicado: 29 de marzo de 2025

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1

Li, Mengjuan, Jingya Li, Zhiguo Zhang, Liming Chen, Nana Ma, Qingfeng Liu, Xingjie Zhang y Guisheng Zhang. "Palladium-catalyzed intramolecular aza-Wacker-type cyclization of vinyl cyclopropanecarboxamides to access conformationally restricted aza[3.1.0]bicycles". RSC Advances 13, n.º 39 (2023): 27158–66. http://dx.doi.org/10.1039/d3ra05440c.

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A palladium(ii)-catalyzed intramolecular oxidative aza-Wacker-type reaction of vinyl cyclopropanecarboxamides to access a series of conformationally restricted highly substituted aza[3.1.0]bicycles is reported.
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2

Thomas, Annu Anna, Someshwar Nagamalla y Shyam Sathyamoorthi. "Salient features of the aza-Wacker cyclization reaction". Chemical Science 11, n.º 31 (2020): 8073–88. http://dx.doi.org/10.1039/d0sc02554b.

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3

Barboza, Amanda Aline, Juliana Arantes Dantas, Guilherme Augusto de Melo Jardim, Marco Antonio Barbosa Ferreira, Mateus Oliveira Costa y Attilio Chiavegatti. "Recent Advances in Palladium-Catalyzed Oxidative Couplings in the Synthesis/Functionalization of Cyclic Scaffolds Using Molecular Oxygen as the Sole Oxidant". Synthesis 54, n.º 09 (19 de noviembre de 2021): 2081–102. http://dx.doi.org/10.1055/a-1701-7397.

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AbstractOver the past years, Pd(II)-catalyzed oxidative couplings have enabled the construction of molecular scaffolds with high structural diversity via C–C, C–N and C–O bond-forming reactions. In contrast to the use of stoichiometric amounts of more common oxidants, such as metal salts (Cu and Ag) and benzoquinone derivatives, the use of molecular oxygen for the direct or indirect regeneration of Pd(II) species presents itself as a more viable alternative in terms of economy and sustainability. In this review, we describe recent advances on the development of Pd-catalyzed oxidative cyclizations/functionalizations, where molecular oxygen plays a pivotal role as the sole stoichiometric oxidant.1 Introduction2 Oxidative C–C and C–Nu Coupling2.1 Intramolecular Oxidative C–Nu Heterocyclization Reactions2.1.1 C–H Activation2.1.2 Wacker/Aza-Wacker-Type Cyclization2.1.3 Tandem Wacker/Aza-Wacker and Cyclization/Cross-Coupling Reactions2.2 Intermolecular Oxidative C–Nu Heterocoupling Reactions2.3 Intramolecular Oxidative (C–C) Carbocyclization Reactions2.4 Intermolecular Oxidative C–C Coupling Reactions2.4.1 Cyclization Reactions2.4.2 Cross-Coupling Reactions2.4.3 Homo-Coupling Reactions3 Aerobic Dehydrogenative Coupling/Functionalization4 Oxidative C–H Functionalization5 Summary
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4

Adachi, Sota y Yohei Okada. "Electrochemical radical cation aza-Wacker cyclizations". Beilstein Journal of Organic Chemistry 20 (5 de agosto de 2024): 1900–1905. http://dx.doi.org/10.3762/bjoc.20.165.

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Electrochemical or photochemical single-electron oxidation of bench-stable substrates can generate radical cations that offer unique reactivities as intermediates in various bond-formation processes. Such intermediates can potentially take part in both radical and ionic bond formation; however, the mechanisms involved are complicated and not fully understood. Herein, we report electrochemical radical cation aza-Wacker cyclizations under acidic conditions, which are expected to proceed via radical cations generated by single-electron oxidation of alkenes.
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5

Youn, So Won y So Ra Lee. "Unusual 1,2-aryl migration in Pd(ii)-catalyzed aza-Wacker-type cyclization of 2-alkenylanilines". Organic & Biomolecular Chemistry 13, n.º 16 (2015): 4652–56. http://dx.doi.org/10.1039/c5ob00361j.

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The discovery of an unprecedented 1,2-aryl migratory process in Pd(ii)-catalyzed aza-Wacker-type cyclization of 2-alkenylanilines that led to a novel synthesis of C3-substituted indoles is demonstrated.
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6

Peng, Xichao y Pengju Feng. "Continuous-Flow Electrochemistry Promoted Aza-Wacker Cyclizations". Chinese Journal of Organic Chemistry 41, n.º 7 (2021): 2918. http://dx.doi.org/10.6023/cjoc202100051.

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7

Wang, Xin, Qinlin Wang, Yanru Xue, Kai Sun, Lanlan Wu y Bing Zhang. "An organoselenium-catalyzed N1- and N2-selective aza-Wacker reaction of alkenes with benzotriazoles". Chemical Communications 56, n.º 32 (2020): 4436–39. http://dx.doi.org/10.1039/d0cc01079k.

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A novel and practical organoselenium-catalyzed, N1- and N2-selective controllable aza-Wacker reaction is realized, which provides an easy access to N1- and N2-olefinated benzotriazole derivatives.
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8

Li, Huimin, Lihao Liao y Xiaodan Zhao. "Organoselenium-Catalyzed Aza-Wacker Reactions: Efficient Access to Isoquinolinium Imides and an Isoquinoline N-Oxide". Synlett 30, n.º 14 (28 de junio de 2019): 1688–92. http://dx.doi.org/10.1055/s-0039-1690103.

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An efficient approach for the organoselenium-catalyzed aza-Wacker reaction of olefinic hydrazones and an oxime to form isoquinolinium imides and an isoquinoline N-oxide is developed. This transformation involves a direct intramolecular C–H amination using hydrazones and an oxime as imine-type nitrogen sources. This work not only provides a new approach for the construction of isoquinoline derivatives, but also expands the scope of nitrogen sources in electrophilic selenium catalysis.
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9

Nagamalla, Someshwar, David K. Johnson y Shyam Sathyamoorthi. "Sulfamate-tethered aza-Wacker approach towards analogs of Bactobolin A". Medicinal Chemistry Research 30, n.º 7 (6 de abril de 2021): 1348–57. http://dx.doi.org/10.1007/s00044-021-02724-7.

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10

Sen, Abhijit, Kazuhiro Takenaka y Hiroaki Sasai. "Enantioselective Aza-Wacker-Type Cyclization Promoted by Pd-SPRIX Catalyst". Organic Letters 20, n.º 21 (24 de octubre de 2018): 6827–31. http://dx.doi.org/10.1021/acs.orglett.8b02946.

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11

Shinde, Anand H., Annu Anna Thomas, Joel T. Mague y Shyam Sathyamoorthi. "Highly Regio- and Diastereoselective Tethered Aza-Wacker Cyclizations of Alkenyl Phosphoramidates". Journal of Organic Chemistry 86, n.º 21 (19 de octubre de 2021): 14732–58. http://dx.doi.org/10.1021/acs.joc.1c01483.

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12

Hu, Huayou, Jiaxin Tian, Yun Liu, Yong Liu, Fei Shi, Xiang Wang, Yuhe Kan y Chao Wang. "Aza-Wacker-Type Reaction between Electron-Deficient Olefins and N-Alkylsulfonamides". Journal of Organic Chemistry 80, n.º 5 (23 de febrero de 2015): 2842–47. http://dx.doi.org/10.1021/jo502823m.

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13

Jiang, Feng, Zhengxing Wu y Wanbin Zhang. "Pd-catalyzed asymmetric aza-Wacker-type cyclization reaction of olefinic tosylamides". Tetrahedron Letters 51, n.º 39 (septiembre de 2010): 5124–26. http://dx.doi.org/10.1016/j.tetlet.2010.07.084.

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14

Elliott, Luke D., Joe W. Wrigglesworth, Brian Cox, Guy C. Lloyd-Jones y Kevin I. Booker-Milburn. "2,2-Difunctionalization of Alkenes via Pd(II)-Catalyzed Aza-Wacker Reactions". Organic Letters 13, n.º 4 (18 de febrero de 2011): 728–31. http://dx.doi.org/10.1021/ol102956x.

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15

Yi, Xiangli y Xile Hu. "Formal Aza‐Wacker Cyclization by Tandem Electrochemical Oxidation and Copper Catalysis". Angewandte Chemie 131, n.º 14 (27 de febrero de 2019): 4748–52. http://dx.doi.org/10.1002/ange.201814509.

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16

Yi, Xiangli y Xile Hu. "Formal Aza‐Wacker Cyclization by Tandem Electrochemical Oxidation and Copper Catalysis". Angewandte Chemie International Edition 58, n.º 14 (27 de febrero de 2019): 4700–4704. http://dx.doi.org/10.1002/anie.201814509.

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17

Allen, Jamie R., Ana Bahamonde, Yukino Furukawa y Matthew S. Sigman. "Enantioselective N-Alkylation of Indoles via an Intermolecular Aza-Wacker-Type Reaction". Journal of the American Chemical Society 141, n.º 22 (22 de mayo de 2019): 8670–74. http://dx.doi.org/10.1021/jacs.9b01476.

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18

Kumar, Manoj, Shalini Verma y Akhilesh K. Verma. "Ru(II)-Catalyzed Oxidative Olefination of Benzamides: Switchable Aza-Michael and Aza-Wacker Reaction for Synthesis of Isoindolinones". Organic Letters 22, n.º 12 (9 de junio de 2020): 4620–26. http://dx.doi.org/10.1021/acs.orglett.0c01237.

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19

Huang, Chong, Zhao‐Yu Li, Jinshuai Song y Hai‐Chao Xu. "Catalyst‐ and Reagent‐Free Formal Aza‐Wacker Cyclizations Enabled by Continuous‐Flow Electrochemistry". Angewandte Chemie International Edition 60, n.º 20 (7 de abril de 2021): 11237–41. http://dx.doi.org/10.1002/anie.202101835.

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20

Huang, Chong, Zhao‐Yu Li, Jinshuai Song y Hai‐Chao Xu. "Catalyst‐ and Reagent‐Free Formal Aza‐Wacker Cyclizations Enabled by Continuous‐Flow Electrochemistry". Angewandte Chemie 133, n.º 20 (7 de abril de 2021): 11337–41. http://dx.doi.org/10.1002/ange.202101835.

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21

Yang, Dong, Jiaming Chen, Yanping Huang, Huiquan Pan, Jingqi Shi, Yingyue Zhang, Fang Wang y Ziyuan Li. "Room-temperature Formal Aza-Wacker Cyclization through Synergistic Copper/TEMPO-catalyzed Radical Relay". ACS Catalysis 11, n.º 15 (21 de julio de 2021): 9860–68. http://dx.doi.org/10.1021/acscatal.1c02721.

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22

Zhang, Zuhui, Jiajing Tan y Zhiyong Wang. "A Facile Synthesis of 2-Methylquinolines via Pd-Catalyzed Aza-Wacker Oxidative Cyclization". Organic Letters 10, n.º 2 (enero de 2008): 173–75. http://dx.doi.org/10.1021/ol702153x.

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23

Zhang, Zuhui, Jintang Zhang, Jiajing Tan y Zhiyong Wang. "A Facile Access to Pyrroles from Amino Acids via an Aza-Wacker Cyclization". Journal of Organic Chemistry 73, n.º 13 (julio de 2008): 5180–82. http://dx.doi.org/10.1021/jo800433b.

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24

Hu, Huayou, Jiaxin Tian, Yun Liu, Yong Liu, Fei Shi, Xiang Wang, Yuhe Kan y Chao Wang. "ChemInform Abstract: Aza-Wacker-Type Reaction Between Electron-Deficient Olefins and N-Alkylsulfonamides." ChemInform 46, n.º 29 (julio de 2015): no. http://dx.doi.org/10.1002/chin.201529113.

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25

Jiang, Feng, Zhengxing Wu y Wanbin Zhang. "ChemInform Abstract: Pd-Catalyzed Asymmetric aza-Wacker-Type Cyclization Reaction of Olefinic Tosylamides." ChemInform 42, n.º 3 (23 de diciembre de 2010): no. http://dx.doi.org/10.1002/chin.201103115.

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26

Elliott, Luke D., Joe W. Wrigglesworth, Brian Cox, Guy C. Lloyd-Jones y Kevin I. Booker-Milburn. "ChemInform Abstract: 2,2-Difunctionalization of Alkenes via Pd(II)-Catalyzed Aza-Wacker Reactions." ChemInform 42, n.º 22 (5 de mayo de 2011): no. http://dx.doi.org/10.1002/chin.201122123.

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27

Barker, David, Benjamin Dickson, Nora Dittrich y Claire E. Rye. "An acyl-Claisen approach to the synthesis of lignans and substituted pyrroles". Pure and Applied Chemistry 84, n.º 7 (25 de marzo de 2012): 1557–65. http://dx.doi.org/10.1351/pac-con-11-09-27.

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The acyl-Claisen rearrangement, also called a zwitterionic aza-Claisen rearrangement, allows for the synthesis of 2,3-syn-substituted morpholine pent-4-eneamides with high levels of diastereoselectivity. A wide variety of alkyl and aryl substituents can be introduced with yields highly dependent on the stoichiometry of the Lewis acid catalyst. The use of these morpholine amides in the synthesis of the tetrasubstituted tetrahydrofuran lignans fragransin A2, talaumidin, and galbelgin is summarized. The conversion of the Claisen-derived amides into aryl tetraline and 1,1-diarylbutanol lignans via alteration of the protecting groups is also described. Nucleophilic addition of an organometallic reagent to the morpholine amide followed by Wacker oxidation of the alkene gives highly substituted 1,4-diketones, which can be easily converted into fully substituted pyrroles.
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28

Allen, Jamie R., Ana Bahamonde, Yukino Furukawa y Matthew S. Sigman. "Correction to “Enantioselective N-Alkylation of Indoles via an Intermolecular Aza-Wacker-Type Reaction”". Journal of the American Chemical Society 141, n.º 31 (26 de julio de 2019): 12420. http://dx.doi.org/10.1021/jacs.9b07380.

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29

Yang, Rui, Jin-Tao Yu, Song Sun, Qingheng Zheng y Jiang Cheng. "Copper-mediated intramolecular aza-Wacker-type cyclization of 2-alkenylanilines toward 3-aryl indoles". Tetrahedron Letters 58, n.º 5 (febrero de 2017): 445–48. http://dx.doi.org/10.1016/j.tetlet.2016.12.053.

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30

Yang, Guoqiang, Chaoren Shen y Wanbin Zhang. "An Asymmetric Aerobic Aza-Wacker-Type Cyclization: Synthesis of Isoindolinones Bearing Tetrasubstituted Carbon Stereocenters". Angewandte Chemie 124, n.º 36 (15 de agosto de 2012): 9275–79. http://dx.doi.org/10.1002/ange.201203693.

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31

Yang, Guoqiang, Chaoren Shen y Wanbin Zhang. "An Asymmetric Aerobic Aza-Wacker-Type Cyclization: Synthesis of Isoindolinones Bearing Tetrasubstituted Carbon Stereocenters". Angewandte Chemie International Edition 51, n.º 36 (15 de agosto de 2012): 9141–45. http://dx.doi.org/10.1002/anie.201203693.

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32

Tang, Rong-Shiow, Li-Yuan Chen, Chin-Hung Lai y Ta-Hsien Chuang. "Palladium-Catalyzed Stereoselective Aza-Wacker–Heck Cyclization: One-Pot Stepwise Strategy toward Tetracyclic Fused Heterocycles". Organic Letters 22, n.º 23 (23 de noviembre de 2020): 9337–41. http://dx.doi.org/10.1021/acs.orglett.0c03552.

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33

Weinstein, Adam B., David P. Schuman, Zhi Xu Tan y Shannon S. Stahl. "Synthesis of Vicinal Aminoalcohols by Stereoselective Aza-Wacker Cyclizations: Access to (−)-Acosamine by Redox Relay". Angewandte Chemie 125, n.º 45 (17 de septiembre de 2013): 12083–86. http://dx.doi.org/10.1002/ange.201305926.

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34

Sen, Abhijit, Linpeng Zhu, Shinobu Takizawa, Kazuhiro Takenaka y Hiroaki Sasai. "Synthesis of Allylamine Derivatives via Intermolecular Aza‐Wacker‐Type Reaction Promoted by Palladium‐SPRIX Catalyst". Advanced Synthesis & Catalysis 362, n.º 17 (14 de julio de 2020): 3558–63. http://dx.doi.org/10.1002/adsc.202000644.

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35

Weinstein, Adam B., David P. Schuman, Zhi Xu Tan y Shannon S. Stahl. "Synthesis of Vicinal Aminoalcohols by Stereoselective Aza-Wacker Cyclizations: Access to (−)-Acosamine by Redox Relay". Angewandte Chemie International Edition 52, n.º 45 (17 de septiembre de 2013): 11867–70. http://dx.doi.org/10.1002/anie.201305926.

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36

Kotov, Vasily, Christopher C. Scarborough y Shannon S. Stahl. "Palladium-Catalyzed Aerobic Oxidative Amination of Alkenes: Development of Intra- and Intermolecular Aza-Wacker Reactions". Inorganic Chemistry 46, n.º 6 (marzo de 2007): 1910–23. http://dx.doi.org/10.1021/ic061997v.

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37

Liu, Guosheng y Shannon S. Stahl. "Two-Faced Reactivity of Alkenes: cis- versustrans-Aminopalladation in Aerobic Pd-Catalyzed Intramolecular Aza-Wacker Reactions". Journal of the American Chemical Society 129, n.º 19 (mayo de 2007): 6328–35. http://dx.doi.org/10.1021/ja070424u.

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38

Yang, Guoqiang y Wanbin Zhang. "Regioselective Pd-Catalyzed Aerobic Aza-Wacker Cyclization for Preparation of Isoindolinones and Isoquinolin-1(2H)-ones". Organic Letters 14, n.º 1 (8 de diciembre de 2011): 268–71. http://dx.doi.org/10.1021/ol203043h.

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39

Yang, Xintuo, Pinhong Chen y Guosheng Liu. "Asymmetric Palladium-Catalyzed Aza-Wacker Reaction of Alkenes: Efficient Synthesis of Chiral 1,3-Oxazinan-2-ones". Chinese Journal of Organic Chemistry 42, n.º 10 (2022): 3382. http://dx.doi.org/10.6023/cjoc202208021.

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40

Yang, Guoqiang, Chaoren Shen y Wanbin Zhang. "ChemInform Abstract: An Asymmetric Aerobic Aza-Wacker-Type Cyclization: Synthesis of Isoindolinones Bearing Tetrasubstituted Carbon Stereocenters." ChemInform 44, n.º 7 (12 de febrero de 2013): no. http://dx.doi.org/10.1002/chin.201307089.

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41

Weinstein, Adam B., David P. Schuman, Zhi Xu Tan y Shannon S. Stahl. "ChemInform Abstract: Synthesis of Vicinal Aminoalcohols by Stereoselective Aza-Wacker Cyclization: Access to (-)-Acosamine by Redox Relay." ChemInform 45, n.º 13 (14 de marzo de 2014): no. http://dx.doi.org/10.1002/chin.201413135.

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42

Youn, So Won y So Ra Lee. "ChemInform Abstract: Unusual 1,2-Aryl Migration in Pd(II)-Catalyzed Aza-Wacker-Type Cyclization of 2-Alkenylanilines." ChemInform 46, n.º 33 (28 de julio de 2015): no. http://dx.doi.org/10.1002/chin.201533156.

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43

White, Paul B., Jonathan N. Jaworski, Geyunjian Harry Zhu y Shannon S. Stahl. "Diazafluorenone-Promoted Oxidation Catalysis: Insights into the Role of Bidentate Ligands in Pd-Catalyzed Aerobic Aza-Wacker Reactions". ACS Catalysis 6, n.º 5 (25 de abril de 2016): 3340–48. http://dx.doi.org/10.1021/acscatal.6b00953.

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44

Yang, Guoqiang y Wanbin Zhang. "ChemInform Abstract: Regioselective Pd-Catalyzed Aerobic Aza-Wacker Cyclization for Preparation of Isoindolinones and Isoquinolin-1(2H)-ones." ChemInform 43, n.º 20 (23 de abril de 2012): no. http://dx.doi.org/10.1002/chin.201220112.

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45

Ye, Chenghao, Xuezhen Kou, Jingzhao Xia, Guoqiang Yang, Li Kong, Quhao Wei y Wanbin Zhang. "PdII -Catalyzed Oxidative Tandem aza-Wacker/Heck Cyclization for the Construction of Fused 5,6-Bicyclic N,O-Heterocycles". Chemistry - An Asian Journal 13, n.º 15 (3 de julio de 2018): 1897–901. http://dx.doi.org/10.1002/asia.201800646.

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46

Bao, Xu, Qian Wang y Jieping Zhu. "Palladium-Catalyzed Enantioselective Desymmetrizing Aza-Wacker Reaction: Development and Application to the Total Synthesis of (−)-Mesembrane and (+)-Crinane". Angewandte Chemie 130, n.º 7 (16 de enero de 2018): 2013–17. http://dx.doi.org/10.1002/ange.201712521.

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47

Bao, Xu, Qian Wang y Jieping Zhu. "Palladium-Catalyzed Enantioselective Desymmetrizing Aza-Wacker Reaction: Development and Application to the Total Synthesis of (−)-Mesembrane and (+)-Crinane". Angewandte Chemie International Edition 57, n.º 7 (16 de enero de 2018): 1995–99. http://dx.doi.org/10.1002/anie.201712521.

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48

Xie, Changmin, Jisheng Luo, Yuping Zhang, Sha-Hua Huang, Lili Zhu y Ran Hong. "Catalytic Aza-Wacker Annulation: Tuning Mechanism by the Activation Mode of Amide and Enantioselective Syntheses of Melinonine-E and Strychnoxanthine". Organic Letters 20, n.º 8 (29 de marzo de 2018): 2386–90. http://dx.doi.org/10.1021/acs.orglett.8b00725.

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49

Ding, Yi, Ye‐Qiang Han, Le‐Song Wu, Tao Zhou, Qi‐Jun Yao, Ya‐Lan Feng, Ya Li, Ke‐Xin Kong y Bing‐Feng Shi. "Pd(II)‐Catalyzed Tandem Enantioselective Methylene C(sp 3 )−H Alkenylation–Aza‐Wacker Cyclization to Access β‐Stereogenic γ‐Lactams". Angewandte Chemie 132, n.º 33 (9 de junio de 2020): 14164–68. http://dx.doi.org/10.1002/ange.202004504.

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50

Ding, Yi, Ye‐Qiang Han, Le‐Song Wu, Tao Zhou, Qi‐Jun Yao, Ya‐Lan Feng, Ya Li, Ke‐Xin Kong y Bing‐Feng Shi. "Pd(II)‐Catalyzed Tandem Enantioselective Methylene C(sp 3 )−H Alkenylation–Aza‐Wacker Cyclization to Access β‐Stereogenic γ‐Lactams". Angewandte Chemie International Edition 59, n.º 33 (9 de junio de 2020): 14060–64. http://dx.doi.org/10.1002/anie.202004504.

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