Iron Phosphate Catalyzed Asymmetric Cross-Dehydrogenative Coupling of 2-Naphthols with β-Ketoesters

This article is cited by 53 publications.

1. Lukas Fliegel, Jens Christoffers. Synthesis of Annulated Benzofuran Derivatives from α-(Iodophenyl)-β-oxoesters. Organic Letters 2022, 24 (46) , 8526-8530. https://doi.org/10.1021/acs.orglett.2c03472
2. Jingze Wu, Marisa C. Kozlowski. Catalytic Oxidative Coupling of Phenols and Related Compounds. ACS Catalysis 2022, 12 (11) , 6532-6549. https://doi.org/10.1021/acscatal.2c00318
3. Alina Dyadyuk, Vlada Vershinin, Hadas Shalit, Hen Shalev, Nagnath Yadav More, Doron Pappo. A Chiral Iron Disulfonate Catalyst for the Enantioselective Synthesis of 2-Amino-2′-hydroxy-1,1′-binaphthyls (NOBINs). Journal of the American Chemical Society 2022, 144 (8) , 3676-3684. https://doi.org/10.1021/jacs.1c13020
4. Tomer Mintz, Nagnath Yadav More, Eden Gaster, Doron Pappo. Iron-Catalyzed Oxidative Cross-Coupling of Phenols and Tyrosine Derivatives with 3-Alkyloxindoles. The Journal of Organic Chemistry 2021, 86 (24) , 18164-18178. https://doi.org/10.1021/acs.joc.1c02435
5. Vlada Vershinin, Hagit Forkosh, Mor Ben-Lulu, Anna Libman, Doron Pappo. Mechanistic Insights into the FeCl3-Catalyzed Oxidative Cross-Coupling of Phenols with 2-Aminonaphthalenes. The Journal of Organic Chemistry 2021, 86 (1) , 79-90. https://doi.org/10.1021/acs.joc.0c00874
6. Masumi Sugawara, Rikako Ohnishi, Tetsuya Ezawa, Mai Akakabe, Miki Sawamura, Daiki Hojo, Daisuke Hashizume, Yoshihiro Sohtome, Mikiko Sodeoka. Regiodivergent Oxidative Cross-Coupling of Catechols with Persistent tert-Carbon Radicals. ACS Catalysis 2020, 10 (21) , 12770-12782. https://doi.org/10.1021/acscatal.0c03986
7. Hagai Reiss, Hadas Shalit, Vlada Vershinin, Nagnath Yadav More, Hagit Forckosh, Doron Pappo. Cobalt(II)[salen]-Catalyzed Selective Aerobic Oxidative Cross-Coupling between Electron-Rich Phenols and 2-Naphthols. The Journal of Organic Chemistry 2019, 84 (12) , 7950-7960. https://doi.org/10.1021/acs.joc.9b00822
8. Hadas Shalit, Alina Dyadyuk, Doron Pappo. Selective Oxidative Phenol Coupling by Iron Catalysis. The Journal of Organic Chemistry 2019, 84 (4) , 1677-1686. https://doi.org/10.1021/acs.joc.8b03084
9. Zheng Huang, Jean-Philip Lumb. Phenol-Directed C–H Functionalization. ACS Catalysis 2019, 9 (1) , 521-555. https://doi.org/10.1021/acscatal.8b04098
10. Hagit Forkosh, Vlada Vershinin, Hagai Reiss, Doron Pappo. Stereoselective Synthesis of Optically Pure 2-Amino-2′-hydroxy-1,1′-binaphthyls. Organic Letters 2018, 20 (8) , 2459-2463. https://doi.org/10.1021/acs.orglett.8b00800
11. Gaurav Shukla, Abhijeet Srivastava, Dhananjay Yadav, and Maya Shankar Singh . Copper-Catalyzed One-Pot Cross-Dehydrogenative Thienannulation: Chemoselective Access to Naphtho[2,1-b]thiophene-4,5-diones and Subsequent Transformation to Benzo[a]thieno[3,2-c]phenazines. The Journal of Organic Chemistry 2018, 83 (4) , 2173-2181. https://doi.org/10.1021/acs.joc.7b03092
12. Agata Dudek and Jacek Mlynarski . Iron-Catalyzed Asymmetric Nitro-Mannich Reaction. The Journal of Organic Chemistry 2017, 82 (20) , 11218-11224. https://doi.org/10.1021/acs.joc.7b01786
13. Evgeny Larionov, Marco M. Mastandrea, and Miquel A. Pericàs . Asymmetric Visible-Light Photoredox Cross-Dehydrogenative Coupling of Aldehydes with Xanthenes. ACS Catalysis 2017, 7 (10) , 7008-7013. https://doi.org/10.1021/acscatal.7b02659
14. Ping Ying, Tao Ying, Hong Chen, Keyu Xiang, Weike Su, Haijiao Xie, Jingbo Yu. Iron-catalyzed asymmetric Csp 3 –H/Csp 3 –H coupling: improving the chirality induction by mechanochemical liquid-assisted grinding. Organic Chemistry Frontiers 2024, 10 https://doi.org/10.1039/D3QO01467C
15. Nian Xu, Maoping Pu, Han Yu, Gaofei Yang, Xiaohua Liu, Xiaoming Feng. Iron‐Catalyzed Asymmetric α‐Alkylation of 2‐Acylimidazoles via Dehydrogenative Radical Cross‐Coupling with Alkanes. Angewandte Chemie International Edition 2023, 565 https://doi.org/10.1002/anie.202314256
16. Nian Xu, Maoping Pu, Han Yu, Gaofei Yang, Xiaohua Liu, Xiaoming Feng. Iron‐Catalyzed Asymmetric α‐Alkylation of 2‐Acylimidazoles via Dehydrogenative Radical Cross‐Coupling with Alkanes. Angewandte Chemie 2023, https://doi.org/10.1002/ange.202314256
17. Ana Maria Faisca Phillips, Armando J. L. Pombeiro. A Mild and Sustainable Procedure for the Functionalization of Morpholin-2-Ones by Oxidative Imidation Reactions. Catalysts 2023, 13 (7) , 1072. https://doi.org/10.3390/catal13071072
18. Lingli Wang, Zhiwei Yao, Wenru Huang, Ting Gao, Pengfei Yan, Yanyan Zhou, Hongfeng Li. Remarkable 980 nm circularly polarized luminescence from dinuclear Yb( iii ) helicates with a D 4 symmetry. Inorganic Chemistry Frontiers 2023, 10 (12) , 3664-3674. https://doi.org/10.1039/D3QI00588G
19. Yanan Li, Yekai Huang, Zhi Li, Jianan Sun. Recent Advances in Regioselective C–H Bond Functionalization of Free Phenols. Molecules 2023, 28 (8) , 3397. https://doi.org/10.3390/molecules28083397
20. He-Ping Li, Xiao-Ling Wu, Gu Zhan, Xue-Ju Fu, Jian-Hua Chen, Xiang-Hong He, Bo Han. Construction of cyclopenta[ b ]dihydronaphthofurans via TsOH-catalyzed consecutive biscyclization of dithioallylic alcohols and 1-styrylnaphthols. Chemical Communications 2023, 59 (16) , 2275-2278. https://doi.org/10.1039/D2CC06324G
21. Sujeet Kumar, Km Kajol, Prakash Nayak, Amit Kumar, Chintakunta Ramesh. Synthesis of tetracyclic 4 H ‐benzo[5,6]chromeno[3,4‐ d ]oxazoles via palladium‐catalyzed intramolecular direct heteroarylation. Chemistry – An Asian Journal 2023, 18 (3) https://doi.org/10.1002/asia.202201151
22. Matthew C. Carson, Marisa C. Kozlowski. Recent advances in oxidative phenol coupling for the total synthesis of natural products. Natural Product Reports 2023, 47 https://doi.org/10.1039/D3NP00009E
23. Jing Liu, Jintao Chen, Tingting Liu, Jia Liu, Yaofu Zeng. Recent Advances in the Reactions of β -Naphthol at α -Position. Chinese Journal of Organic Chemistry 2023, 43 (2) , 379. https://doi.org/10.6023/cjoc202207015
24. Tristan von Münchow, Yanjun Li, Zi-Jing Zhang, Philipp Boos, Lutz Ackermann. Carbon–Carbon Bond Formation by Asymmetric Iron- and Cobalt-Catalyzed Reactions. 2023https://doi.org/10.1016/B978-0-32-390644-9.00119-0
25. Sobi Asako, Laurean Ilies. Iron‐Catalyzed Enantioselective CH Functionalization. 2022, 1-15. https://doi.org/10.1002/9783527834242.chf0137
26. Fan Jia, Zhiping Li. Iron‐Catalyzed Cross‐Dehydrogenative Coupling. 2022, 1-24. https://doi.org/10.1002/9783527834242.chf0046
27. Hanqiang Jia, Min He, Shilei Yang, Xiaoqiang Yu, Ming Bao. Visible‐Light‐Driven di‐ t ‐Butyl Peroxide‐Promoted the Oxidative Homo‐ and Cross‐Coupling of Phenols. European Journal of Organic Chemistry 2022, 2022 (8) https://doi.org/10.1002/ejoc.202101469
28. Makoto Sako, Keigo Higashida, Ganesh Tatya Kamble, Kevin Kaut, Ankit Kumar, Yuka Hirose, Da-Yang Zhou, Takeyuki Suzuki, Magnus Rueping, Tomohiro Maegawa, Shinobu Takizawa, Hiroaki Sasai. Chemo- and enantioselective hetero-coupling of hydroxycarbazoles catalyzed by a chiral vanadium( v ) complex. Organic Chemistry Frontiers 2021, 8 (17) , 4878-4885. https://doi.org/10.1039/D1QO00783A
29. Xigong Liu, Changyin Zhao, Rongxiu Zhu, Lei Liu. Construction of Vicinal Quaternary Carbon Stereocenters Through Diastereo‐ and Enantioselective Oxidative 1,6‐Conjugate Addition. Angewandte Chemie 2021, 133 (34) , 18647-18651. https://doi.org/10.1002/ange.202105594
30. Xigong Liu, Changyin Zhao, Rongxiu Zhu, Lei Liu. Construction of Vicinal Quaternary Carbon Stereocenters Through Diastereo‐ and Enantioselective Oxidative 1,6‐Conjugate Addition. Angewandte Chemie International Edition 2021, 60 (34) , 18499-18503. https://doi.org/10.1002/anie.202105594
31. So Won Youn, Cheon-Gyu Cho. Transition-metal-catalyzed ortho -selective C–H functionalization reactions of free phenols. Organic & Biomolecular Chemistry 2021, 19 (23) , 5028-5047. https://doi.org/10.1039/D1OB00506E
32. Takahiro Horibe, Masato Sakakibara, Rin Hiramatsu, Kazuki Takeda, Kazuaki Ishihara. One‐Pot Tandem Michael Addition/Enantioselective Conia‐Ene Cyclization Mediated by Chiral Iron(III)/Silver(I) Cooperative Catalysis. Angewandte Chemie 2020, 132 (38) , 16612-16616. https://doi.org/10.1002/ange.202007180
33. Takahiro Horibe, Masato Sakakibara, Rin Hiramatsu, Kazuki Takeda, Kazuaki Ishihara. One‐Pot Tandem Michael Addition/Enantioselective Conia‐Ene Cyclization Mediated by Chiral Iron(III)/Silver(I) Cooperative Catalysis. Angewandte Chemie International Edition 2020, 59 (38) , 16470-16474. https://doi.org/10.1002/anie.202007180
34. Kexu Zhou, Ying Yu, Yu-Mei Lin, Yanjun Li, Lei Gong. Copper-catalyzed aerobic asymmetric cross-dehydrogenative coupling of C(sp 3 )–H bonds driven by visible light. Green Chemistry 2020, 22 (14) , 4597-4603. https://doi.org/10.1039/D0GC00262C
35. Tao Jiang, Yikang Tu, Zijian Su, Manman Lu, Shuo Liu, Jicheng Liu, Foquan Gu, Yuanbo Zhang. A novel value-added utilization process for pyrite cinder: Selective recovery of Cu/Co and synthesis of iron phosphate. Hydrometallurgy 2020, 193 , 105314. https://doi.org/10.1016/j.hydromet.2020.105314
36. Ana Maria Faisca Phillips, Maria de Fátima C. Guedes da Silva, Armando J. L. Pombeiro. New Trends in Enantioselective Cross-Dehydrogenative Coupling. Catalysts 2020, 10 (5) , 529. https://doi.org/10.3390/catal10050529
37. X.P. Brannmijk. BNP, bnp. 2020https://doi.org/10.1002/9783527809080.cataz02222
38. Mor Ben‐Lulu, Eden Gaster, Anna Libman, Doron Pappo. Synthesis of Biaryl‐Bridged Cyclic Peptides via Catalytic Oxidative Cross‐Coupling Reactions. Angewandte Chemie 2020, 132 (12) , 4865-4869. https://doi.org/10.1002/ange.201913305
39. Mor Ben‐Lulu, Eden Gaster, Anna Libman, Doron Pappo. Synthesis of Biaryl‐Bridged Cyclic Peptides via Catalytic Oxidative Cross‐Coupling Reactions. Angewandte Chemie International Edition 2020, 59 (12) , 4835-4839. https://doi.org/10.1002/anie.201913305
40. Na Li, Liang Tu, Guiguang Cheng, Houling Sa, Zhenghui Li, Tao Feng, Yongsheng Zheng, Jikai Liu. Diastereoselective [3 + 3] cycloaddition reaction of 2-arylideneindan-1,3-diones with β-naphthols: Efficient assemble of immunosuppressive pentacyclic chromanes. Tetrahedron Letters 2020, 61 (10) , 151579. https://doi.org/10.1016/j.tetlet.2019.151579
41. Zehua Wang, Yasheng Zhu, Xiaoguang Pan, Gang Wang, Lei Liu. Synthesis of Chiral Triarylmethanes Bearing All‐Carbon Quaternary Stereocenters: Catalytic Asymmetric Oxidative Cross‐Coupling of 2,2‐Diarylacetonitriles and (Hetero)arenes. Angewandte Chemie 2020, 132 (8) , 3077-3081. https://doi.org/10.1002/ange.201912739
42. Zehua Wang, Yasheng Zhu, Xiaoguang Pan, Gang Wang, Lei Liu. Synthesis of Chiral Triarylmethanes Bearing All‐Carbon Quaternary Stereocenters: Catalytic Asymmetric Oxidative Cross‐Coupling of 2,2‐Diarylacetonitriles and (Hetero)arenes. Angewandte Chemie International Edition 2020, 59 (8) , 3053-3057. https://doi.org/10.1002/anie.201912739
43. Gang Wang, Xiaodong Xin, Zehua Wang, Gang Lu, Yudao Ma, Lei Liu. Catalytic enantioselective oxidative coupling of saturated ethers with carboxylic acid derivatives. Nature Communications 2019, 10 (1) https://doi.org/10.1038/s41467-019-08473-x
44. Gui-Chun Fang, Yong-Feng Cheng, Zhang-Long Yu, Zhong-Liang Li, Xin-Yuan Liu. Recent Advances in First-Row Transition Metal/Chiral Phosphoric Acid Combined Catalysis. Topics in Current Chemistry 2019, 377 (5) https://doi.org/10.1007/s41061-019-0249-0
45. Adarsh Krishna T.P, Sakthivel Pandaram, Andivelu Ilangovan. Iron-mediated site-selective oxidative C–H/C–H cross-coupling of aryl radicals with quinones: synthesis of β-secretase-1 inhibitor B and related arylated quinones. Organic Chemistry Frontiers 2019, 6 (18) , 3244-3251. https://doi.org/10.1039/C9QO00623K
46. Shingo Harada, Chigaya Sakai, Koki Tanikawa, Tetsuhiro Nemoto. Gold-catalyzed chemoselective formal (3+2)-Annulation reaction between β-naphthols and methyl aryldiazoacetate. Tetrahedron 2019, 75 (26) , 3650-3656. https://doi.org/10.1016/j.tet.2019.05.040
47. Hélène Pellissier. Recent developments in enantioselective iron-catalyzed transformations. Coordination Chemistry Reviews 2019, 386 , 1-31. https://doi.org/10.1016/j.ccr.2019.01.011
48. Haorui Gu, Shaoying Huang, Xufeng Lin. Iron-catalyzed asymmetric intramolecular cyclopropanation reactions using chiral tetramethyl-1,1′-spirobiindane-based bisoxazoline (TMSI-BOX) ligands. Organic & Biomolecular Chemistry 2019, 17 (5) , 1154-1162. https://doi.org/10.1039/C8OB03065K
49. Ahmad A. Almasalma, Esteban Mejía. Mechanistic Pathways Toward the Synthesis of Heterocycles Under Cross-Dehydrogenative Conditions. 2019, 329-356. https://doi.org/10.1007/978-981-13-9144-6_10
50. Dhananjay Yadav, Gaurav Shukla, Monish A. Ansari, Abhijeet Srivastava, Maya Shankar Singh. Chemoselective one-pot access to benzo[e]indole-4,5-diones and naphtho[2,1-b]thiophene-4,5-diones via copper-catalyzed oxidative [3 + 2] annulation of α-oxoketene N,S-acetals/β-ketothioamides with α-/β-naphthols. Tetrahedron 2018, 74 (40) , 5920-5931. https://doi.org/10.1016/j.tet.2018.08.026
51. Xianzhen Song, Ying Cao, Yi Zhang, Fangjing Sun, Xixi Yan, Xiaoyu Liu, Lijun Wang. Preparation and characterization of nanoscale flaky iron phosphate from phosphating slag. IOP Conference Series: Materials Science and Engineering 2018, 397 , 012001. https://doi.org/10.1088/1757-899X/397/1/012001
52. Phongprapan Nimnual, Krissada Norseeda, Bhornrawin Akkachairin, Jumreang Tummatorn, Pavitra Laohapaisan, Nantamon Supantanapong, Pennapa Chuangsoongnern, Charnsak Thongsornkleeb, Satapanawat Sittihan, Somsak Ruchirawat, Warabhorn Rodphon. Synthesis of β‐Naphthols and Naphthofuranones from ortho ‐Alkynylarylketones via Sequential AgTFA‐Catalyzed Ketonization–Intramolecular Aldol Condensation: A Total Synthesis of Negundin A. Asian Journal of Organic Chemistry 2018, 7 (5) , 932-945. https://doi.org/10.1002/ajoc.201800025
53. Eike B. Bauer. Recent Advances in Iron Catalyzed Oxidation Reactions of Organic Compounds. Israel Journal of Chemistry 2017, 57 (12) , 1131-1150. https://doi.org/10.1002/ijch.201700050