Palladium-Catalyzed Direct Arylation of Heteroaromatic Compounds: Improved Conditions Utilizing Controlled Microwave Heating

Click to copy article linkArticle link copied!

This article is cited by 119 publications.

1. Rohan Kalyan Rej, Junius Eugene Thomas II, Ranjan Kumar Acharyya, James Michael Rae, Shaomeng Wang. Targeting the Estrogen Receptor for the Treatment of Breast Cancer: Recent Advances and Challenges. Journal of Medicinal Chemistry 2023, 66 (13) , 8339-8381. https://doi.org/10.1021/acs.jmedchem.3c00136
2. Markus Baenziger, Marcel Baierl, Krishnaswamy Devanathan, Sumesh Eswaran, Peng Fu, Bjoern Gschwend, Michael Haller, Gopu Kasinathan, Nikola Kovacic, Audrey Langlois, Yongfeng Li, Friedrich Schuerch, Xiaodong Shen, Yinbo Wan, Regina Wickendick, Siwei Xie, Kai Zhang. Synthesis Development of the Selective Estrogen Receptor Degrader (SERD) LSZ102 from a Suzuki Coupling to a C–H Activation Strategy. Organic Process Research & Development 2020, 24 (8) , 1405-1419. https://doi.org/10.1021/acs.oprd.0c00076
3. Renu Bhaskar, Alpesh K. Sharma, Ajai K. Singh. Palladium(II) Complexes of N-Heterocyclic Carbene Amidates Derived from Chalcogenated Acetamide-Functionalized 1H-Benzimidazolium Salts: Recyclable Catalyst for Regioselective Arylation of Imidazoles under Aerobic Conditions. Organometallics 2018, 37 (16) , 2669-2681. https://doi.org/10.1021/acs.organomet.8b00246
4. Chiara Colletto, Adyasha Panigrahi, Jaime Fernández-Casado, Igor Larrosa. Ag(I)–C–H Activation Enables Near-Room-Temperature Direct α-Arylation of Benzo[b]thiophenes. Journal of the American Chemical Society 2018, 140 (30) , 9638-9643. https://doi.org/10.1021/jacs.8b05361
5. Li-Qun Hu, Rong-Li Deng, Yan-Fen Li, Cui-Jin Zeng, Dong-Sheng Shen, and Feng-Shou Liu . Developing Bis(imino)acenaphthene-Supported N-Heterocyclic Carbene Palladium Precatalysts for Direct Arylation of Azoles. Organometallics 2018, 37 (2) , 214-226. https://doi.org/10.1021/acs.organomet.7b00784
6. Roman A. Novikov, Anna V. Tarasova, Dmitry A. Denisov, Denis D. Borisov, Victor A. Korolev, Vladimir P. Timofeev, and Yury V. Tomilov . [4 + 2] Annulation of Donor–Acceptor Cyclopropanes with Acetylenes Using 1,2-Zwitterionic Reactivity. The Journal of Organic Chemistry 2017, 82 (5) , 2724-2738. https://doi.org/10.1021/acs.joc.7b00209
7. Juan Wei, Kun-Ming Liu, and Xin-Fang Duan . Cobalt-Catalyzed Biaryl Couplings via C–F Bond Activation in the Absence of Phosphine or NHC Ligands. The Journal of Organic Chemistry 2017, 82 (3) , 1291-1300. https://doi.org/10.1021/acs.joc.6b02354
8. Xu-Xian He, Yinwu Li, Bei-Bei Ma, Zhuofeng Ke, and Feng-Shou Liu . Sterically Encumbered Tetraarylimidazolium Carbene Pd-PEPPSI Complexes: Highly Efficient Direct Arylation of Imidazoles with Aryl Bromides under Aerobic Conditions. Organometallics 2016, 35 (16) , 2655-2663. https://doi.org/10.1021/acs.organomet.6b00391
9. Thomas Bura, J. Terence Blaskovits, and Mario Leclerc . Direct (Hetero)arylation Polymerization: Trends and Perspectives. Journal of the American Chemical Society 2016, 138 (32) , 10056-10071. https://doi.org/10.1021/jacs.6b06237
10. Min Sik Eom, Jieun Noh, Han-Sung Kim, Soyeon Yoo, Min Su Han, and Sunwoo Lee . High-Throughput Screening Protocol for the Coupling Reactions of Aryl Halides Using a Colorimetric Chemosensor for Halide Ions. Organic Letters 2016, 18 (8) , 1720-1723. https://doi.org/10.1021/acs.orglett.6b00300
11. Chiara Colletto, Saidul Islam, Francisco Juliá-Hernández, and Igor Larrosa . Room-Temperature Direct β-Arylation of Thiophenes and Benzo[b]thiophenes and Kinetic Evidence for a Heck-type Pathway. Journal of the American Chemical Society 2016, 138 (5) , 1677-1683. https://doi.org/10.1021/jacs.5b12242
12. Yabo Li, Jingran Wang, Mengmeng Huang, Zhiwei Wang, Yusheng Wu, and Yangjie Wu . Direct C–H Arylation of Thiophenes at Low Catalyst Loading of a Phosphine-Free Bis(alkoxo)palladium Complex. The Journal of Organic Chemistry 2014, 79 (7) , 2890-2897. https://doi.org/10.1021/jo402745b
13. Maxwell J. Robb, Damien Montarnal, Nancy D. Eisenmenger, Sung-Yu Ku, Michael L. Chabinyc, and Craig J. Hawker . A One-Step Strategy for End-Functionalized Donor–Acceptor Conjugated Polymers. Macromolecules 2013, 46 (16) , 6431-6438. https://doi.org/10.1021/ma401255d
14. Seong Jib Choi, Junpei Kuwabara, and Takaki Kanbara . Microwave-Assisted Polycondensation via Direct Arylation of 3,4-Ethylenedioxythiophene with 9,9-Dioctyl-2,7-dibromofluorene. ACS Sustainable Chemistry & Engineering 2013, 1 (8) , 878-882. https://doi.org/10.1021/sc4000576
15. C. Oliver Kappe . Unraveling the Mysteries of Microwave Chemistry Using Silicon Carbide Reactor Technology. Accounts of Chemical Research 2013, 46 (7) , 1579-1587. https://doi.org/10.1021/ar300318c
16. Theresa M. McCormick, Colin R. Bridges, Elisa I. Carrera, Paul M. DiCarmine, Gregory L. Gibson, Jon Hollinger, Lisa M. Kozycz, and Dwight S. Seferos . Conjugated Polymers: Evaluating DFT Methods for More Accurate Orbital Energy Modeling. Macromolecules 2013, 46 (10) , 3879-3886. https://doi.org/10.1021/ma4005023
17. Binjie Liu, Yong Fan, Xiaoming Lv, Xiaofeng Liu, Yongtai Yang, and Yu Jia . Generation and Reactions of Heteroaromatic Lithium Compounds by Using In-Line Mixer in a Continuous Flow Microreactor System at Mild Conditions. Organic Process Research & Development 2013, 17 (1) , 133-137. https://doi.org/10.1021/op300205j
18. Debalina Ghosh and Hon Man Lee . Efficient Pd-Catalyzed Direct Arylations of Heterocycles with Unreactive and Hindered Aryl Chlorides. Organic Letters 2012, 14 (21) , 5534-5537. https://doi.org/10.1021/ol302635e
19. Emilien Demory, Daniel Farran, Benoit Baptiste, Pierre Y. Chavant, and Véronique Blandin . Fast Pd- and Pd/Cu-Catalyzed Direct C–H Arylation of Cyclic Nitrones. Application to the Synthesis of Enantiopure Quaternary α-Amino Esters. The Journal of Organic Chemistry 2012, 77 (18) , 7901-7912. https://doi.org/10.1021/jo301114k
20. Sebastian Kowalski, Sybille Allard, and Ullrich Scherf . Synthesis of Poly(4,4-dialkyl-cyclopenta[2,1-b:3,4-b′]dithiophene-alt-2,1,3-benzothiadiazole) (PCPDTBT) in a Direct Arylation Scheme. ACS Macro Letters 2012, 1 (4) , 465-468. https://doi.org/10.1021/mz300093w
21. Abhishek Sharma, Dipak Vachhani, and Erik Van der Eycken . Direct Heteroarylation of Tautomerizable Heterocycles into Unsymmetrical and Symmetrical Biheterocycles via Pd/Cu-Catalyzed Phosphonium Coupling. Organic Letters 2012, 14 (7) , 1854-1857. https://doi.org/10.1021/ol300455e
22. Murat Kaloğlu, Namık Özdemir, İsmail Özdemir. 4,5‐Dihydro‐imidazol‐2‐ylidene‐linked palladium complexes as catalysts for the direct CH bond arylation of azoles. Applied Organometallic Chemistry 2024, 38 (10) https://doi.org/10.1002/aoc.6551
23. Tuba Fırat, Nesrin Buğday, Şeyma Yaşar, Houssem Boulebd, Lamjed Mansour, Waleed S. Koko, Naceur Hamdi, Sedat Yaşar. Bridged NHC-Pd(II) complexes: Synthesis, DFT calculations, molecular docking, and investigation of catalytic and biological activities. Journal of Organometallic Chemistry 2024, 1011 , 123129. https://doi.org/10.1016/j.jorganchem.2024.123129
24. Mahmood Tajbakhsh, Fatemeh Mazhari, Negar Nirouei. Preparation and characterization of sulfamic acid-functionalized Fe3O4 nanoparticles as an efficient magnetic nanocatalyst for the facile and eco-friendly synthesis of quinoxalines, benzothiazoles, and benzoxazoles. Research on Chemical Intermediates 2024, 50 (3) , 1287-1311. https://doi.org/10.1007/s11164-023-05214-0
25. Daniele Malpicci, Silvia Rosa Araneo, Serena Arnaboldi, Elena Cariati, Alessandra Forni, Sara Grecchi, Elena Lucenti, Daniele Marinotto, Daniele Maver, Patrizia Romana Mussini. Electrochemical insight on the nitrogen-rich, weakly aromatic cyclic triimidazole multifunctional system expanded with pyridine or thiophene terminals. Electrochimica Acta 2023, 469 , 143117. https://doi.org/10.1016/j.electacta.2023.143117
26. Jung Min Joo. Functionalization of Five‐membered Heterocycles with Two Heteroatoms. 2023, 109-154. https://doi.org/10.1002/9781119774167.ch3
27. Madhusudan K. Pandey, Sachin C. Sonawane, Dipanjan Mondal, Basvaraj S. Kote, Maravanji S. Balakrishna. Palladium(II) Complexes of (2,6‐Dibenzhydryl‐4‐methylphenyl)diphenyl‐phosphane: Synthesis, Structural Studies, and Catalytic Arylation of Imidazoles Under Aerobic Conditions. European Journal of Inorganic Chemistry 2022, 2022 (33) https://doi.org/10.1002/ejic.202200447
28. Murat Kaloğlu, Mehmet Hanifi Şahan, Serpil Demir Düşünceli, İsmail Özdemir. Synthesis of Quinoxaline-Linked Bis(Benzimidazolium) Salts and Their Catalytic Application in Palladium-Catalyzed Direct Arylation of Heteroarenes. Catalysis Letters 2022, 152 (7) , 2012-2024. https://doi.org/10.1007/s10562-021-03787-2
29. Km Kajol, Sujeet Kumar, Amit Kumar, Ruchir Kant, Chintakunta Ramesh. Palladium‐Catalyzed Intramolecular C−H Heteroarylation to Access Fused Tricyclic Oxazolo[4,5‐c]Quinolines. Asian Journal of Organic Chemistry 2022, 11 (4) https://doi.org/10.1002/ajoc.202200066
30. Gianluigi Albano, Angela Punzi, Maria Annunziata M. Capozzi, Gianluca M. Farinola. Sustainable protocols for direct C–H bond arylation of (hetero)arenes. Green Chemistry 2022, 24 (5) , 1809-1894. https://doi.org/10.1039/D1GC03168F
31. Gianluigi Albano, Gianfranco Decandia, Maria Annunziata M. Capozzi, Nicola Zappimbulso, Angela Punzi, Gianluca M. Farinola. Infrared Irradiation‐Assisted Solvent‐Free Pd‐Catalyzed (Hetero)aryl‐aryl Coupling via C−H Bond Activation. ChemSusChem 2021, 14 (16) , 3391-3401. https://doi.org/10.1002/cssc.202101070
32. Ashraf A. El-Shehawy, Morad M. El-Hendawy, Adel M. Attia, Abdul-Rahman I. A. Abdallah, Nabiha I. Abdo. Synthesis, photophysical properties, and computational studies of benzothiadiazole and/or phenothiazine based donor/acceptor π-conjugated copolymers. Journal of Polymer Research 2021, 28 (7) https://doi.org/10.1007/s10965-021-02621-y
33. Marco Lessi, Attilio Nania, Melania Pittari, Laura Lodone, Angela Cuzzola, Fabio Bellina. Palladium-Catalyzed Dehydrogenative C-2 Alkenylation of 5-Arylimidazoles and Related Azoles with Styrenes. Catalysts 2021, 11 (7) , 762. https://doi.org/10.3390/catal11070762
34. Siraj Khan, Nesrin Buğday, Sedat Yaşar, Naseem Ullah, İsmail Özdemir. Pd-N-heterocyclic carbene complex catalysed C–H bond activation of 2-isobutylthiazole at the C5 position with aryl bromides. New Journal of Chemistry 2021, 45 (14) , 6281-6292. https://doi.org/10.1039/D1NJ00514F
35. Nesrin Buğday, Siraj Khan, Sedat Yaşar, İsmail Özdemir. C H Bond activation of 2-isobutylthiazole at C5 position catalysed by Pd-N-heterocyclic carbene complexes. Journal of Organometallic Chemistry 2021, 937 , 121730. https://doi.org/10.1016/j.jorganchem.2021.121730
36. Dewal S. Deshmukh, Vaishali S. Shende, Bhalchandra M. Bhanage. Insights into Sustainable C–H Bond Activation. 2021, 253-318. https://doi.org/10.1007/978-3-030-65021-6_8
37. Rammyani Pal, Chhanda Mukhopadhyay. Microwave-assisted Carbon-carbon and Carbon-heteroatom Cross-coupling Reactions in Organic Synthesis. Current Microwave Chemistry 2020, 7 (2) , 86-98. https://doi.org/10.2174/2213335607666200310121337
38. Bishnu Prasad Raiguru, Sabita Nayak, Deepak Ranjan Mishra, Tapaswini Das, Seetaram Mohapatra, Nilima Priyadarsini Mishra. Synthetic Applications of Cyclopropene and Cyclopropenone: Recent Progress and Developments. Asian Journal of Organic Chemistry 2020, 9 (8) , 1088-1132. https://doi.org/10.1002/ajoc.202000193
39. Kevin H. Shaughnessy. Monodentate Trialkylphosphines: Privileged Ligands in Metal-catalyzed Crosscoupling Reactions. Current Organic Chemistry 2020, 24 (3) , 231-264. https://doi.org/10.2174/1385272824666200211114540
40. Kevin Padberg, Johannes D. R. Ascherl, Frank Hampel, Milan Kivala. Isomeric Dithienophosphepines: The Impact of Ring Fusion on Electronic and Structural Properties. Chemistry – A European Journal 2020, 26 (16) , 3474-3478. https://doi.org/10.1002/chem.201905429
41. Jhen‐Yi Lee, Debalina Ghosh, Ya‐Ting Kuo, Hon Man Lee. Dimetallic Palladium‐NHC Complexes: Synthesis, Characterization, and Catalytic Application for Direct C−H Arylation Reaction of Heteroaromatics with Aryl Chlorides. Advanced Synthesis & Catalysis 2020, 362 (3) , 648-658. https://doi.org/10.1002/adsc.201901189
42. N. Yoshikai, C. M. Rayner, M. A. Graham. 10.4 Product Class 4: Benzo[b]thiophenes. 2020https://doi.org/10.1055/sos-SD-110-01749
43. Bei-Bei Ma, Xiao-Bing Lan, Dong-Sheng Shen, Feng-Shou Liu, Chang Xu. Direct C-H bond (Hetero)arylation of thiazole derivatives at 5-position catalyzed by N-heterocyclic carbene palladium complexes at low catalyst loadings under aerobic conditions. Journal of Organometallic Chemistry 2019, 897 , 13-22. https://doi.org/10.1016/j.jorganchem.2019.06.016
44. Masahiro Tsukao, Yoshifumi Hashikawa, Nana Toyama, Masahiro Muraoka, Michihisa Murata, Takahiro Sasamori, Atsushi Wakamiya, Yasujiro Murata. Propeller-Shaped Aluminum Complexes with an Azaperylene Core in the Ligands. Inorganics 2019, 7 (9) , 109. https://doi.org/10.3390/inorganics7090109
45. Nikolay A. Bumagin, Sergey K. Petkevich, Alexey V. Kletskov, Roman S. Alekseyev, Vladimir I. Potkin. Effective bimetallic composite catalysts for the synthesis of arylated furans and thiophenes in aqueous media. Chemistry of Heterocyclic Compounds 2019, 55 (6) , 508-516. https://doi.org/10.1007/s10593-019-02492-8
46. C. Oliver Kappe. My Twenty Years in Microwave Chemistry: From Kitchen Ovens to Microwaves that aren't Microwaves. The Chemical Record 2019, 19 (1) , 15-39. https://doi.org/10.1002/tcr.201800045
47. Haoqiang Zhao, Jianbin Xu, Changjun Chen, Xin Xu, Yixiao Pan, Zongyao Zhang, Huanrong Li, Lijin Xu. Rhodium(III)‐Catalyzed Selective Direct Olefination of Imidazoles. Advanced Synthesis & Catalysis 2018, 360 (5) , 985-994. https://doi.org/10.1002/adsc.201701515
48. Xiaoming Wang, Andreas Lerchen, Constantin G. Daniliuc, Frank Glorius. Effiziente Synthese von arylierten Furanen durch sequentielle Rhodium‐katalysierte Arylierung und Cycloisomerisierung von Cyclopropenen. Angewandte Chemie 2018, 130 (6) , 1728-1732. https://doi.org/10.1002/ange.201712019
49. Xiaoming Wang, Andreas Lerchen, Constantin G. Daniliuc, Frank Glorius. Efficient Synthesis of Arylated Furans by a Sequential Rh‐Catalyzed Arylation and Cycloisomerization of Cyclopropenes. Angewandte Chemie International Edition 2018, 57 (6) , 1712-1716. https://doi.org/10.1002/anie.201712019
50. Jia Wen, Yinghua Lv, Pengyi Xia, Fengyu Liu, Yongqian Xu, Hongjuan Li, Su-Shing Chen, Shiguo Sun. A water-soluble near-infrared fluorescent probe for specific Pd2+ detection. Bioorganic & Medicinal Chemistry 2018, 26 (4) , 931-937. https://doi.org/10.1016/j.bmc.2017.12.003
51. Hyeongwoo Kim, Ye Ji Hwang, Inhyuk Han, Jung Min Joo. Regioselective C–H alkenylation of imidazoles and its application to the synthesis of unsymmetrically substituted benzimidazoles. Chemical Communications 2018, 54 (50) , 6879-6882. https://doi.org/10.1039/C8CC02405G
52. Rabab Boyaala, Rachid Touzani, Véronique Guerchais, Jean-François Soulé, Henri Doucet. Synthesis of 2-(fluorinated aryl)pyridine derivatives via palladium-catalyzed C H bond arylation of fluorobenzenes using 2-halopyridines as aryl sources. Tetrahedron Letters 2017, 58 (33) , 3205-3208. https://doi.org/10.1016/j.tetlet.2017.06.075
53. Shun-Chao Yin, Quan Zhou, Qian-Wei He, Shu-Wan Li, Peng-Cheng Qian, Li-Xiong Shao. N-Heterocyclic carbene-Pd(II)-1-methylimidazole complex catalyzed C H bond arylation of (benzo)thiophenes with aryl chlorides. Tetrahedron 2017, 73 (5) , 427-431. https://doi.org/10.1016/j.tet.2016.11.053
54. Fu-Min Chen, Dong-Dong Lu, Li-Qun Hu, Ju Huang, Feng-Shou Liu. Camphyl-based α-diimine palladium complexes: highly efficient precatalysts for direct arylation of thiazoles in open-air. Organic & Biomolecular Chemistry 2017, 15 (27) , 5731-5736. https://doi.org/10.1039/C7OB00856B
55. Mohd Sani Sarjadi, Ahmed Iraqi. Synthesis of Carbazole Based Co-polymers Containing Thienothiophene and Benzothiadiazole Units in a Direct Arylation Scheme. Polymers and Polymer Composites 2016, 24 (9) , 703-710. https://doi.org/10.1177/096739111602400905
56. Luca Alessandro Perego, Laurence Grimaud, Fabio Bellina. Mechanistic Studies on the Palladium‐Catalyzed Direct C‐5 Arylation of Imidazoles: The Fundamental Role of the Azole as a Ligand for Palladium. Advanced Synthesis & Catalysis 2016, 358 (4) , 597-609. https://doi.org/10.1002/adsc.201500888
57. Xiao-Xi He, Yan-Fang Li, Ju Huang, Dong-Sheng Shen, Feng-Shou Liu. A convenient phosphine-free palladium-catalyzed direct arylation of thiazole under mild aerobic conditions. Journal of Organometallic Chemistry 2016, 803 , 58-66. https://doi.org/10.1016/j.jorganchem.2015.12.009
58. Raysa Khan, Robert Felix, Paul D. Kemmitt, Simon J. Coles, Iain J. Day, Graham J. Tizzard, John Spencer. Late Stage CH Activation of a Privileged Scaffold; Synthesis of a Library of Benzodiazepines. Advanced Synthesis & Catalysis 2016, 358 (1) , 98-109. https://doi.org/10.1002/adsc.201501009
59. Charles Beromeo Bheeter, Lu Chen, Jean-François Soulé, Henri Doucet. Regioselectivity in palladium-catalysed direct arylation of 5-membered ring heteroaromatics. Catalysis Science & Technology 2016, 6 (7) , 2005-2049. https://doi.org/10.1039/C5CY02095F
60. Wided Hagui, Néji Besbes, Ezzeddine Srasra, Jean-François Soulé, Henri Doucet. Direct access to 2-(hetero)arylated pyridines from 6-substituted 2-bromopyridines via phosphine-free palladium-catalyzed C–H bond arylations: the importance of the C6 substituent. RSC Advances 2016, 6 (21) , 17110-17117. https://doi.org/10.1039/C6RA01861K
61. Roman A. Irgashev, Nikita A. Kazin, Grigory A. Kim, Gennady L. Rusinov, Valery N. Charushin. A new synthetic approach to fused nine-ring systems of the indolo[3,2-b]carbazole family through double Pd-catalyzed intramolecular C–H arylation. RSC Advances 2016, 6 (74) , 70106-70116. https://doi.org/10.1039/C6RA11796A
62. D. Spitzner. 15.1.4 Pyridines (Update 2016). 2016https://doi.org/10.1055/sos-SD-115-00035
63. Xiaowen Xu, Liqin Zhao, Yiqun Li, Jean‐François Soulé, Henri Doucet. Intermolecular versus Intramolecular Palladium‐Catalyzed Direct Arylations between 1‐(2‐Bromobenzyl)imidazoles and Aryl Bromides. Advanced Synthesis & Catalysis 2015, 357 (13) , 2869-2882. https://doi.org/10.1002/adsc.201500332
64. Vanessa Prieur, M. Dolors Pujol, Gérald Guillaumet. A Strategy for the Triarylation of Pyrrolo­pyrimidines by Using Microwave‐Promoted Cross‐Coupling Reactions. European Journal of Organic Chemistry 2015, 2015 (29) , 6547-6556. https://doi.org/10.1002/ejoc.201500625
65. Natsuyo Kamimoto, Dieter Schollmeyer, Koichi Mitsudo, Seiji Suga, Siegfried R. Waldvogel. Palladium‐Catalyzed Domino CH/NH Functionalization: An Efficient Approach to Nitrogen‐Bridged Heteroacenes. Chemistry – A European Journal 2015, 21 (22) , 8257-8261. https://doi.org/10.1002/chem.201500897
66. Lorena Navarro, M. Dolors Pujol. Microwave assisted synthesis of selected diaryl ethers under Cu(I)-catalysis. Tetrahedron Letters 2015, 56 (14) , 1812-1815. https://doi.org/10.1016/j.tetlet.2015.02.073
67. Vanessa Prieur, Nina Heindler, Jaime Rubio-Martínez, Gérald Guillaumet, M. Dolors Pujol. One-pot synthesis of 4-aminated pyrrolo[2,3-d]pyrimidines from alkynylpyrimidines under metal-catalyst-free conditions. Tetrahedron 2015, 71 (8) , 1207-1214. https://doi.org/10.1016/j.tet.2015.01.012
68. Alysson Duarte Rodrigues, Thibaut Imberdis, Véronique Perrier, Mike Robitzer. Improved synthesis of a quaterthiophene-triazine-diamine derivative, a promising molecule to study pathogenic prion proteins. Tetrahedron Letters 2015, 56 (2) , 368-373. https://doi.org/10.1016/j.tetlet.2014.11.098
69. Saïd El Kazzouli, Jamal Koubachi, Nabil El Brahmi, Gérald Guillaumet. Advances in direct C–H arylation of 5,5- 6,5- and 6,6-fused-heterocycles containing heteroatoms (N, O, S). RSC Advances 2015, 5 (20) , 15292-15327. https://doi.org/10.1039/C4RA15384G
70. Toan Dao‐Huy, Maximilian Haider, Fabian Glatz, Michael Schnürch, Marko D. Mihovilovic. Direct Arylation of Benzo[ b ]furan and Other Benzo‐Fused Heterocycles. European Journal of Organic Chemistry 2014, 2014 (36) , 8119-8125. https://doi.org/10.1002/ejoc.201403125
71. Mohammad Ali Zolfigol, Ardeshir Khazaei, Negin Sarmasti, Jaber Yousefi Seyf, Vahid Khakyzadeh, Ahmad Reza Moosavi-Zare. Programming of microwave-assisted synthesis of new isophthalate derivatives using ZrOCl2 as a catalyst under solvent-free condition by experimental design. Journal of Molecular Catalysis A: Chemical 2014, 393 , 142-149. https://doi.org/10.1016/j.molcata.2014.06.014
72. Giuseppe Marzano, Cosimo V. Ciasca, Francesco Babudri, Gabriele Bianchi, Andrea Pellegrino, Riccardo Po, Gianluca M. Farinola. Organometallic Approaches to Conjugated Polymers for Plastic Solar Cells: From Laboratory Synthesis to Industrial Production. European Journal of Organic Chemistry 2014, 2014 (30) , 6583-6614. https://doi.org/10.1002/ejoc.201402226
73. Margherita Durso, Massimo Zambianchi, Alberto Zanelli, M. Grazia LoBello, Filippo De Angelis, Stefano Toffanin, Susanna Cavallini, Denis Gentili, Francesca Tinti, Massimiliano Cavallini, Nadia Camaioni, Manuela Melucci. Synthesis by MW-assisted direct arylation, side-arms driven self-assembly and functional properties of 9,10-dithienylanthracene orthogonal materials. Tetrahedron 2014, 70 (36) , 6222-6228. https://doi.org/10.1016/j.tet.2014.03.010
74. V. I. Potkin, N. A. Bumagin, V. M. Zelenkovskii, S. K. Petkevich, M. V. Livantsov, N. E. Golantsov. 5-(Naphth-1-yl)- and 5-[(1,1′-biphenyl)-4-yl]isoxazole-3-carbaldehyde oximes: Synthesis, complexes with palladium, and application in catalysis. Russian Journal of General Chemistry 2014, 84 (9) , 1782-1792. https://doi.org/10.1134/S1070363214090242
75. Qiufeng Huang, Shaojia Ke, Lin Qiu, Xiaofeng Zhang, Shen Lin. Palladium(II)/Polyoxometalate‐Catalyzed Direct Alkenylation of Benzofurans under Atmospheric Dioxygen. ChemCatChem 2014, 6 (6) , 1531-1534. https://doi.org/10.1002/cctc.201400091
76. Esa T. T. Kumpulainen, Antti Pohjakallio. Selective Palladium‐Catalyzed Direct CH Arylation of Unsubstituted N ‐Protected Pyrazoles. Advanced Synthesis & Catalysis 2014, 356 (7) , 1555-1561. https://doi.org/10.1002/adsc.201301139
77. N. A. Bumagin, I. S. Veselov, D. S. Belov. An Effective Activation of Palladium Phosphine Complexes in Aqueous Phase Reactions of Hetero-Aromatic Boronic Acids with Aryl Halides. Chemistry of Heterocyclic Compounds 2014, 50 (1) , 19-25. https://doi.org/10.1007/s10593-014-1443-1
78. Vanessa Prieur, Jaime Rubio‐Martínez, Mercè Font‐Bardia, Gérald Guillaumet, M. Dolors Pujol. Microwave‐Assisted Synthesis of Substituted Pyrrolo[2,3‐ d ]pyrimidines. European Journal of Organic Chemistry 2014, 2014 (7) , 1514-1524. https://doi.org/10.1002/ejoc.201301496
79. Sara Zamanian, Ali Nemati Kharat. Cyanoethylation of alcohols and amines by cesium-modified zeolite Y. Chinese Journal of Catalysis 2014, 35 (2) , 264-269. https://doi.org/10.1016/S1872-2067(12)60751-7
80. Junichiro Yamaguchi, Kenichiro Itami. Biaryl Synthesis through Metal‐Catalyzed C–H Arylation. 2014, 1315-1387. https://doi.org/10.1002/9783527655588.ch17
81. Renzo Rossi, Fabio Bellina, Marco Lessi, Chiara Manzini. Cross‐Coupling of Heteroarenes by CH Functionalization: Recent Progress towards Direct Arylation and Heteroarylation Reactions Involving Heteroarenes Containing One Heteroatom. Advanced Synthesis & Catalysis 2014, 356 (1) , 17-117. https://doi.org/10.1002/adsc.201300922
82. Nicholas E. Leadbeater. Microwave-Assisted Synthesis: General Concepts. 2014, 1-44. https://doi.org/10.1007/12_2013_274
83. Zoltán Novák, András Kotschy. Synthesis and Transformations of Oxygen Heterocycles. 2014, 231-303. https://doi.org/10.1007/7081_2014_136
84. N.E. Leadbeater. 9.10 Organic Synthesis Using Microwave Heating. 2014, 234-286. https://doi.org/10.1016/B978-0-08-097742-3.00920-4
85. György M. Keserű, Tibor Soós, C. Oliver Kappe. Anthropogenic reaction parameters – the missing link between chemical intuition and the available chemical space. Chem. Soc. Rev. 2014, 43 (15) , 5387-5399. https://doi.org/10.1039/C3CS60423C
86. Julija Kudrjasova, Roald Herckens, Huguette Penxten, Peter Adriaensens, Laurence Lutsen, Dirk Vanderzande, Wouter Maes. Direct arylation as a versatile tool towards thiazolo[5,4-d]thiazole-based semiconducting materials. Org. Biomol. Chem. 2014, 12 (26) , 4663-4672. https://doi.org/10.1039/C4OB00360H
87. Alexandre Bruneau, Jean-Daniel Brion, Samir Messaoudi, Mouad Alami. A general Pd/Cu-catalyzed C–H heteroarylation of 3-bromoquinolin-2(1H)-ones. Org. Biomol. Chem. 2014, 12 (42) , 8533-8541. https://doi.org/10.1039/C4OB01610F
88. Pedro Blas González, Jay Zumbar Chandanshive, Mariafrancesca Fochi, Bianca Flavia Bonini, Andrea Mazzanti, Luca Bernardi, Erica Locatelli, Lorenzo Caruana, Claudio Monasterolo, Mauro Comes Franchini. Experimental and Computational Investigation of the 1,3‐Dipolar Cycloaddition of the Ynamide tert ‐Butyl N ‐Ethynyl‐ N ‐phenylcarbamate with C ‐Carboxymethyl‐ N ‐phenylnitrilimine. European Journal of Organic Chemistry 2013, 2013 (36) , 8108-8114. https://doi.org/10.1002/ejoc.201301054
89. S. Kowalski, S. Allard, K. Zilberberg, T. Riedl, U. Scherf. Direct arylation polycondensation as simplified alternative for the synthesis of conjugated (co)polymers. Progress in Polymer Science 2013, 38 (12) , 1805-1814. https://doi.org/10.1016/j.progpolymsci.2013.04.006
90. David Obermayer, Markus Damm, C. Oliver Kappe. Simulating Microwave Chemistry in a Resistance‐Heated Autoclave Made of Semiconducting Silicon Carbide Ceramic. Chemistry – A European Journal 2013, 19 (47) , 15827-15830. https://doi.org/10.1002/chem.201303638
91. Eul Kgun Yum, Ok-Kyung Yang, Ji-Eun Kim, Hee Jung Park. Synthesis of 2-Substituted Benzofurans from o-Iodophenols and Terminal Alkynes with a Recyclable Palladium Catalyst Supported on Nano-sized Carbon Balls under Copper- and Ligand-Free Conditions. Bulletin of the Korean Chemical Society 2013, 34 (9) , 2645-2649. https://doi.org/10.5012/bkcs.2013.34.9.2645
92. Fabio Bellina, Marco Lessi, Chiara Manzini. Mild Palladium‐Catalyzed Regioselective Direct Arylation of Azoles Promoted by Tetrabutylammonium Acetate. European Journal of Organic Chemistry 2013, 2013 (25) , 5621-5630. https://doi.org/10.1002/ejoc.201300704
93. Peter Ehlers, Andranik Petrosyan, Jens Baumgard, Stefan Jopp, Norbert Steinfeld, Tariel V. Ghochikyan, Ashot S. Saghyan, Christine Fischer, Peter Langer. Synthesis of 2,5‐Diarylpyrroles by Ligand‐Free Palladium‐Catalyzed CH Activation of Pyrroles in Ionic Liquids. ChemCatChem 2013, 5 (8) , 2504-2511. https://doi.org/10.1002/cctc.201300099
94. Liqin Zhao, Christian Bruneau, Henri Doucet. Phosphine-free palladium-catalysed direct C2-arylation of benzothiophenes with aryl bromides. Tetrahedron 2013, 69 (34) , 7082-7089. https://doi.org/10.1016/j.tet.2013.06.037
95. Lu Chen, Christian Bruneau, Pierre H. Dixneuf, Henri Doucet. Palladium-acetate catalyst for regioselective direct arylation at C2 of 3-furanyl or 3-thiophenyl acrylates with inhibition of Heck type reaction. Tetrahedron 2013, 69 (22) , 4381-4388. https://doi.org/10.1016/j.tet.2012.12.061
96. Egor V. Verbitskiy, Ekaterina M. Cheprakova, Ekaterina F. Zhilina, Mikhail I. Kodess, Marina A. Ezhikova, Marina G. Pervova, Pavel A. Slepukhin, Julia O. Subbotina, Aleksandr V. Schepochkin, Gennady L. Rusinov, Oleg N. Chupakhin, Valery N. Charushin. Microwave-assisted palladium-catalyzed C–C coupling versus nucleophilic aromatic substitution of hydrogen (SNH) in 5-bromopyrimidine by action of bithiophene and its analogues. Tetrahedron 2013, 69 (25) , 5164-5172. https://doi.org/10.1016/j.tet.2013.04.062
97. Abhishek Sharma, Dipak Vacchani, Erik Van der Eycken. Developments in Direct CH Arylation of (Hetero)Arenes under Microwave Irradiation. Chemistry – A European Journal 2013, 19 (4) , 1158-1168. https://doi.org/10.1002/chem.201201868
98. Ko Hoon Kim, Jin Woo Lim, Hyun Ju Lee, Jae Nyoung Kim. Palladium-catalyzed arylation of methyl 2-(acetoxymethyl)acrylate: a convenient synthesis of rearranged Morita–Baylis–Hillman acetates. Tetrahedron Letters 2013, 54 (5) , 419-423. https://doi.org/10.1016/j.tetlet.2012.11.026
99. Se Hee Kim, Ko Hoon Kim, Hyun Ju Lee, Jae Nyoung Kim. An expedient synthesis of 3-arylmethylbutenolides from α-methylene-γ-butyrolactones: a useful synthetic application of palladium-catalyzed chelation-controlled oxidative arylation protocol. Tetrahedron Letters 2013, 54 (4) , 329-334. https://doi.org/10.1016/j.tetlet.2012.11.040
100. D. J. C. Prasad, G. Sekar. Cu-catalyzed in situ generation of thiol using xanthate as a thiol surrogate for the one-pot synthesis of benzothiazoles and benzothiophenes. Organic & Biomolecular Chemistry 2013, 11 (10) , 1659. https://doi.org/10.1039/c3ob26915a