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Journal articles on the topic 'Aza-Wacker'

Author: Grafiati

Published: 29 March 2025

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1

Li, Mengjuan, Jingya Li, Zhiguo Zhang, Liming Chen, Nana Ma, Qingfeng Liu, Xingjie Zhang, and Guisheng Zhang. "Palladium-catalyzed intramolecular aza-Wacker-type cyclization of vinyl cyclopropanecarboxamides to access conformationally restricted aza[3.1.0]bicycles." RSC Advances 13, no. 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, and Shyam Sathyamoorthi. "Salient features of the aza-Wacker cyclization reaction." Chemical Science 11, no. 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, and 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, no. 09 (November 19, 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, and Yohei Okada. "Electrochemical radical cation aza-Wacker cyclizations." Beilstein Journal of Organic Chemistry 20 (August 5, 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, and So Ra Lee. "Unusual 1,2-aryl migration in Pd(ii)-catalyzed aza-Wacker-type cyclization of 2-alkenylanilines." Organic & Biomolecular Chemistry 13, no. 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, and Pengju Feng. "Continuous-Flow Electrochemistry Promoted Aza-Wacker Cyclizations." Chinese Journal of Organic Chemistry 41, no. 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, and Bing Zhang. "An organoselenium-catalyzed N1- and N2-selective aza-Wacker reaction of alkenes with benzotriazoles." Chemical Communications 56, no. 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, and Xiaodan Zhao. "Organoselenium-Catalyzed Aza-Wacker Reactions: Efficient Access to Isoquinolinium Imides and an Isoquinoline N-Oxide." Synlett 30, no. 14 (June 28, 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, and Shyam Sathyamoorthi. "Sulfamate-tethered aza-Wacker approach towards analogs of Bactobolin A." Medicinal Chemistry Research 30, no. 7 (April 6, 2021): 1348–57. http://dx.doi.org/10.1007/s00044-021-02724-7.

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10

Sen, Abhijit, Kazuhiro Takenaka, and Hiroaki Sasai. "Enantioselective Aza-Wacker-Type Cyclization Promoted by Pd-SPRIX Catalyst." Organic Letters 20, no. 21 (October 24, 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, and Shyam Sathyamoorthi. "Highly Regio- and Diastereoselective Tethered Aza-Wacker Cyclizations of Alkenyl Phosphoramidates." Journal of Organic Chemistry 86, no. 21 (October 19, 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, and Chao Wang. "Aza-Wacker-Type Reaction between Electron-Deficient Olefins and N-Alkylsulfonamides." Journal of Organic Chemistry 80, no. 5 (February 23, 2015): 2842–47. http://dx.doi.org/10.1021/jo502823m.

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13

Jiang, Feng, Zhengxing Wu, and Wanbin Zhang. "Pd-catalyzed asymmetric aza-Wacker-type cyclization reaction of olefinic tosylamides." Tetrahedron Letters 51, no. 39 (September 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, and Kevin I. Booker-Milburn. "2,2-Difunctionalization of Alkenes via Pd(II)-Catalyzed Aza-Wacker Reactions." Organic Letters 13, no. 4 (February 18, 2011): 728–31. http://dx.doi.org/10.1021/ol102956x.

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15

Yi, Xiangli, and Xile Hu. "Formal Aza‐Wacker Cyclization by Tandem Electrochemical Oxidation and Copper Catalysis." Angewandte Chemie 131, no. 14 (February 27, 2019): 4748–52. http://dx.doi.org/10.1002/ange.201814509.

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16

Yi, Xiangli, and Xile Hu. "Formal Aza‐Wacker Cyclization by Tandem Electrochemical Oxidation and Copper Catalysis." Angewandte Chemie International Edition 58, no. 14 (February 27, 2019): 4700–4704. http://dx.doi.org/10.1002/anie.201814509.

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17

Allen, Jamie R., Ana Bahamonde, Yukino Furukawa, and Matthew S. Sigman. "Enantioselective N-Alkylation of Indoles via an Intermolecular Aza-Wacker-Type Reaction." Journal of the American Chemical Society 141, no. 22 (May 22, 2019): 8670–74. http://dx.doi.org/10.1021/jacs.9b01476.

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18

Kumar, Manoj, Shalini Verma, and Akhilesh K. Verma. "Ru(II)-Catalyzed Oxidative Olefination of Benzamides: Switchable Aza-Michael and Aza-Wacker Reaction for Synthesis of Isoindolinones." Organic Letters 22, no. 12 (June 9, 2020): 4620–26. http://dx.doi.org/10.1021/acs.orglett.0c01237.

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19

Huang, Chong, Zhao‐Yu Li, Jinshuai Song, and Hai‐Chao Xu. "Catalyst‐ and Reagent‐Free Formal Aza‐Wacker Cyclizations Enabled by Continuous‐Flow Electrochemistry." Angewandte Chemie International Edition 60, no. 20 (April 7, 2021): 11237–41. http://dx.doi.org/10.1002/anie.202101835.

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20

Huang, Chong, Zhao‐Yu Li, Jinshuai Song, and Hai‐Chao Xu. "Catalyst‐ and Reagent‐Free Formal Aza‐Wacker Cyclizations Enabled by Continuous‐Flow Electrochemistry." Angewandte Chemie 133, no. 20 (April 7, 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, and Ziyuan Li. "Room-temperature Formal Aza-Wacker Cyclization through Synergistic Copper/TEMPO-catalyzed Radical Relay." ACS Catalysis 11, no. 15 (July 21, 2021): 9860–68. http://dx.doi.org/10.1021/acscatal.1c02721.

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22

Zhang, Zuhui, Jiajing Tan, and Zhiyong Wang. "A Facile Synthesis of 2-Methylquinolines via Pd-Catalyzed Aza-Wacker Oxidative Cyclization." Organic Letters 10, no. 2 (January 2008): 173–75. http://dx.doi.org/10.1021/ol702153x.

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23

Zhang, Zuhui, Jintang Zhang, Jiajing Tan, and Zhiyong Wang. "A Facile Access to Pyrroles from Amino Acids via an Aza-Wacker Cyclization." Journal of Organic Chemistry 73, no. 13 (July 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, and Chao Wang. "ChemInform Abstract: Aza-Wacker-Type Reaction Between Electron-Deficient Olefins and N-Alkylsulfonamides." ChemInform 46, no. 29 (July 2015): no. http://dx.doi.org/10.1002/chin.201529113.

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25

Jiang, Feng, Zhengxing Wu, and Wanbin Zhang. "ChemInform Abstract: Pd-Catalyzed Asymmetric aza-Wacker-Type Cyclization Reaction of Olefinic Tosylamides." ChemInform 42, no. 3 (December 23, 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, and Kevin I. Booker-Milburn. "ChemInform Abstract: 2,2-Difunctionalization of Alkenes via Pd(II)-Catalyzed Aza-Wacker Reactions." ChemInform 42, no. 22 (May 5, 2011): no. http://dx.doi.org/10.1002/chin.201122123.

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27

Barker, David, Benjamin Dickson, Nora Dittrich, and Claire E. Rye. "An acyl-Claisen approach to the synthesis of lignans and substituted pyrroles." Pure and Applied Chemistry 84, no. 7 (March 25, 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, and Matthew S. Sigman. "Correction to “Enantioselective N-Alkylation of Indoles via an Intermolecular Aza-Wacker-Type Reaction”." Journal of the American Chemical Society 141, no. 31 (July 26, 2019): 12420. http://dx.doi.org/10.1021/jacs.9b07380.

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29

Yang, Rui, Jin-Tao Yu, Song Sun, Qingheng Zheng, and Jiang Cheng. "Copper-mediated intramolecular aza-Wacker-type cyclization of 2-alkenylanilines toward 3-aryl indoles." Tetrahedron Letters 58, no. 5 (February 2017): 445–48. http://dx.doi.org/10.1016/j.tetlet.2016.12.053.

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30

Yang, Guoqiang, Chaoren Shen, and Wanbin Zhang. "An Asymmetric Aerobic Aza-Wacker-Type Cyclization: Synthesis of Isoindolinones Bearing Tetrasubstituted Carbon Stereocenters." Angewandte Chemie 124, no. 36 (August 15, 2012): 9275–79. http://dx.doi.org/10.1002/ange.201203693.

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31

Yang, Guoqiang, Chaoren Shen, and Wanbin Zhang. "An Asymmetric Aerobic Aza-Wacker-Type Cyclization: Synthesis of Isoindolinones Bearing Tetrasubstituted Carbon Stereocenters." Angewandte Chemie International Edition 51, no. 36 (August 15, 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, and Ta-Hsien Chuang. "Palladium-Catalyzed Stereoselective Aza-Wacker–Heck Cyclization: One-Pot Stepwise Strategy toward Tetracyclic Fused Heterocycles." Organic Letters 22, no. 23 (November 23, 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, and Shannon S. Stahl. "Synthesis of Vicinal Aminoalcohols by Stereoselective Aza-Wacker Cyclizations: Access to (−)-Acosamine by Redox Relay." Angewandte Chemie 125, no. 45 (September 17, 2013): 12083–86. http://dx.doi.org/10.1002/ange.201305926.

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34

Sen, Abhijit, Linpeng Zhu, Shinobu Takizawa, Kazuhiro Takenaka, and Hiroaki Sasai. "Synthesis of Allylamine Derivatives via Intermolecular Aza‐Wacker‐Type Reaction Promoted by Palladium‐SPRIX Catalyst." Advanced Synthesis & Catalysis 362, no. 17 (July 14, 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, and Shannon S. Stahl. "Synthesis of Vicinal Aminoalcohols by Stereoselective Aza-Wacker Cyclizations: Access to (−)-Acosamine by Redox Relay." Angewandte Chemie International Edition 52, no. 45 (September 17, 2013): 11867–70. http://dx.doi.org/10.1002/anie.201305926.

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36

Kotov, Vasily, Christopher C. Scarborough, and Shannon S. Stahl. "Palladium-Catalyzed Aerobic Oxidative Amination of Alkenes: Development of Intra- and Intermolecular Aza-Wacker Reactions." Inorganic Chemistry 46, no. 6 (March 2007): 1910–23. http://dx.doi.org/10.1021/ic061997v.

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37

Liu, Guosheng, and 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, no. 19 (May 2007): 6328–35. http://dx.doi.org/10.1021/ja070424u.

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38

Yang, Guoqiang, and Wanbin Zhang. "Regioselective Pd-Catalyzed Aerobic Aza-Wacker Cyclization for Preparation of Isoindolinones and Isoquinolin-1(2H)-ones." Organic Letters 14, no. 1 (December 8, 2011): 268–71. http://dx.doi.org/10.1021/ol203043h.

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39

Yang, Xintuo, Pinhong Chen, and 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, no. 10 (2022): 3382. http://dx.doi.org/10.6023/cjoc202208021.

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40

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

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41

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

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42

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

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43

White, Paul B., Jonathan N. Jaworski, Geyunjian Harry Zhu, and Shannon S. Stahl. "Diazafluorenone-Promoted Oxidation Catalysis: Insights into the Role of Bidentate Ligands in Pd-Catalyzed Aerobic Aza-Wacker Reactions." ACS Catalysis 6, no. 5 (April 25, 2016): 3340–48. http://dx.doi.org/10.1021/acscatal.6b00953.

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44

Yang, Guoqiang, and Wanbin Zhang. "ChemInform Abstract: Regioselective Pd-Catalyzed Aerobic Aza-Wacker Cyclization for Preparation of Isoindolinones and Isoquinolin-1(2H)-ones." ChemInform 43, no. 20 (April 23, 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, and 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, no. 15 (July 3, 2018): 1897–901. http://dx.doi.org/10.1002/asia.201800646.

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46

Bao, Xu, Qian Wang, and Jieping Zhu. "Palladium-Catalyzed Enantioselective Desymmetrizing Aza-Wacker Reaction: Development and Application to the Total Synthesis of (−)-Mesembrane and (+)-Crinane." Angewandte Chemie 130, no. 7 (January 16, 2018): 2013–17. http://dx.doi.org/10.1002/ange.201712521.

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47

Bao, Xu, Qian Wang, and 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, no. 7 (January 16, 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, and 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, no. 8 (March 29, 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, and 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, no. 33 (June 9, 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, and 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, no. 33 (June 9, 2020): 14060–64. http://dx.doi.org/10.1002/anie.202004504.

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