Nickel-Catalyzed Reduction of Secondary and Tertiary Amides

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2. Vinothkumar Vinayagam, Subir Kumar Sadhukhan, Satish Kumar Karre, Ravuri Srinath, Ravi Kumar Maroju, Purushotham Reddy Karra, Hema Sundar Naveen Babu Bathula, Siva Kundrapu, Srikanth Reddy Surukonti. TBAT-Catalyzed Deoxygenative Reduction of Tertiary Amides to Amines. Organic Letters 2023, 25 (25) , 4610-4614. https://doi.org/10.1021/acs.orglett.3c01150
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4. Hao Song, Yao Xiao, Zhuohua Zhang, Wanjin Xiong, Ren Wang, Liangcheng Guo, Taigang Zhou. Switching Selectivity in Copper-Catalyzed Transfer Hydrogenation of Nitriles to Primary Amine-Boranes and Secondary Amines under Mild Conditions. The Journal of Organic Chemistry 2022, 87 (1) , 790-800. https://doi.org/10.1021/acs.joc.1c02413
5. Adam Cook, Haydn MacLean, Piers St. Onge, Stephen G. Newman. Nickel-Catalyzed Reductive Deoxygenation of Diverse C–O Bond-Bearing Functional Groups. ACS Catalysis 2021, 11 (21) , 13337-13347. https://doi.org/10.1021/acscatal.1c03980
6. Zhili Wang, Weifeng Chu, Zhenchao Zhao, Zhengmao Liu, Hongyu Chen, Dong Xiao, Ke Gong, Fan Li, Xiujie Li, Guangjin Hou. The Role of Organic and Inorganic Structure-Directing Agents in Selective Al Substitution of Zeolite. The Journal of Physical Chemistry Letters 2021, 12 (38) , 9398-9406. https://doi.org/10.1021/acs.jpclett.1c01448
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8. Adam Cook, Sekar Prakash, Yan-Long Zheng, Stephen G. Newman. Exhaustive Reduction of Esters Enabled by Nickel Catalysis. Journal of the American Chemical Society 2020, 142 (18) , 8109-8115. https://doi.org/10.1021/jacs.0c02405
9. Zejin Song, Jing Zeng, Ting Li, Xiang Zhao, Jing Fang, Lingkui Meng, Qian Wan. Water Compatible Hypophosphites-d2 Reagents: Deuteration Reaction via Deutero-deiodination in Aqueous Solution. Organic Letters 2020, 22 (5) , 1736-1741. https://doi.org/10.1021/acs.orglett.0c00001
10. Pengqing Ye, Yinlin Shao, Xuanzeng Ye, Fangjun Zhang, Renhao Li, Jiani Sun, Beihang Xu, Jiuxi Chen. Homoleptic Bis(trimethylsilyl)amides of Yttrium Complexes Catalyzed Hydroboration Reduction of Amides to Amines. Organic Letters 2020, 22 (4) , 1306-1310. https://doi.org/10.1021/acs.orglett.9b04606
11. Andrei V. Iosub, Štefan Moravčík, Carl-Johan Wallentin, Joakim Bergman. Nickel-Catalyzed Selective Reduction of Carboxylic Acids to Aldehydes. Organic Letters 2019, 21 (19) , 7804-7808. https://doi.org/10.1021/acs.orglett.9b02779
12. Joyann S. Barber, Stephanie Scales, Michelle Tran-Dubé, Fen Wang, Neal W. Sach, Louise Bernier, Michael R. Collins, JinJiang Zhu, Indrawan J. McAlpine, Ryan L. Patman. Rhodium(III)-Catalyzed C–H Activation: Ligand-Controlled Regioselective Synthesis of 4-Methyl-Substituted Dihydroisoquinolones. Organic Letters 2019, 21 (14) , 5689-5693. https://doi.org/10.1021/acs.orglett.9b02029
13. Michael T. Peruzzi, Fabrice Gallou, Stephen J. Lee, Michel R. Gagné. Site Selective Amide Reduction of Cyclosporine A Enables Diverse Derivation of an Important Cyclic Peptide. Organic Letters 2019, 21 (9) , 3451-3455. https://doi.org/10.1021/acs.orglett.9b01245
14. Benedicta Assoah, Luis F. Veiros, Nuno R. Candeias. Pinacol-Derived Chlorohydrosilane in Metal-Free Reductive Amination for the Preparation of Tertiary Alkylphenolmethyl Amines. Organic Letters 2019, 21 (5) , 1402-1406. https://doi.org/10.1021/acs.orglett.9b00121
15. Xu Zhu, Christopher C. McAtee, Corinna S. Schindler. Total Syntheses of Herqulines B and C. Journal of the American Chemical Society 2019, 141 (8) , 3409-3413. https://doi.org/10.1021/jacs.8b13849
16. Sem Raj Tamang, Arpita Singh, Daniel K. Unruh, Michael Findlater. Nickel-Catalyzed Regioselective 1,4-Hydroboration of N-Heteroarenes. ACS Catalysis 2018, 8 (7) , 6186-6191. https://doi.org/10.1021/acscatal.8b01166
17. Marian C. Bryan, , Louis Diorazio, , Zhongbo Fei, , Kenneth Fraunhoffer, , John Hayler, , Matthew Hickey, , Shaun Hughes, , Mark McLaws, , Paul Richardson, , Gheorghe-Doru Roiban, , Markus Schober, , Austin G. Smith, , Alan Steven, , Timothy White, , Stijn Wuyts, , Jingjun Yin. Green Chemistry Articles of Interest to the Pharmaceutical Industry. Organic Process Research & Development 2018, 22 (6) , 667-680. https://doi.org/10.1021/acs.oprd.8b00056
18. Xiangqian Liu, Chien-Chi Hsiao, Lin Guo, Magnus Rueping. Cross-Coupling of Amides with Alkylboranes via Nickel-Catalyzed C–N Bond Cleavage. Organic Letters 2018, 20 (10) , 2976-2979. https://doi.org/10.1021/acs.orglett.8b01021
19. Jijun Chen, Wenhao Long, Yonggang Yang, Xiaobing Wan. Interception of Secondary Amide Ylide with Sulfonamides: Catalyst-Controlled Synthesis of N-Sulfonylamidine Derivatives. Organic Letters 2018, 20 (9) , 2663-2666. https://doi.org/10.1021/acs.orglett.8b00867
20. Guangni Ding, Xiaoyu Wu, Lili Jiang, Zhaoguo Zhang, and Xiaomin Xie . Reduction of Benzolactams to Isoindoles via an Alkoxide-Catalyzed Hydrosilylation. Organic Letters 2017, 19 (22) , 6048-6051. https://doi.org/10.1021/acs.orglett.7b02739
21. Daria Grosheva and Nicolai Cramer . Ketene Aminal Phosphates: Competent Substrates for Enantioselective Pd(0)-Catalyzed C–H Functionalizations. ACS Catalysis 2017, 7 (11) , 7417-7420. https://doi.org/10.1021/acscatal.7b02783
22. Chong-Lei Ji and Xin Hong . Factors Controlling the Reactivity and Chemoselectivity of Resonance Destabilized Amides in Ni-Catalyzed Decarbonylative and Nondecarbonylative Suzuki-Miyaura Coupling. Journal of the American Chemical Society 2017, 139 (43) , 15522-15529. https://doi.org/10.1021/jacs.7b09482
23. Adisak Chatupheeraphat, Hsuan-Hung Liao, Shao-Chi Lee, and Magnus Rueping . Nickel-Catalyzed C–CN Bond Formation via Decarbonylative Cyanation of Esters, Amides, and Intramolecular Recombination Fragment Coupling of Acyl Cyanides. Organic Letters 2017, 19 (16) , 4255-4258. https://doi.org/10.1021/acs.orglett.7b01905
24. Watchara Srimontree, Adisak Chatupheeraphat, Hsuan-Hung Liao, and Magnus Rueping . Amide to Alkyne Interconversion via a Nickel/Copper-Catalyzed Deamidative Cross-Coupling of Aryl and Alkenyl Amides. Organic Letters 2017, 19 (12) , 3091-3094. https://doi.org/10.1021/acs.orglett.7b01194
25. Ya‐Kui Sun, Jin‐Bao Qiao, Yu‐Meng Xin, Qin Zhou, Zhi‐Hua Ma, Hui Shao, Yu‐Ming Zhao. Total Synthesis of Metaphanine and Oxoepistephamiersine. Angewandte Chemie 2023, 135 (40) https://doi.org/10.1002/ange.202310917
26. Ya‐Kui Sun, Jin‐Bao Qiao, Yu‐Meng Xin, Qin Zhou, Zhi‐Hua Ma, Hui Shao, Yu‐Ming Zhao. Total Synthesis of Metaphanine and Oxoepistephamiersine. Angewandte Chemie International Edition 2023, 62 (40) https://doi.org/10.1002/anie.202310917
27. Jiamin Huang, Feixiang Sun, Weiping Liu. Manganese-catalyzed deoxygenation of secondary and tertiary amides under mild conditions. Journal of Catalysis 2023, 423 , 19-25. https://doi.org/10.1016/j.jcat.2023.04.012
28. Bhushan A. Baviskar, Prashant V. Ajmire, Deshraj S. Chumbhale, Mohammad Sadat Khan, Vitthal G. Kuchake, Madhavi Singupuram, Purushottam R. Laddha. Recent advances in nickel catalyzed Suzuki-Miyaura cross coupling reaction via C-O& C-N bond activation. Sustainable Chemistry and Pharmacy 2023, 32 , 100953. https://doi.org/10.1016/j.scp.2022.100953
29. Karthik S. Iyer, Chandler Nelson, Bruce H. Lipshutz. Facile, green, and functional group-tolerant reductions of carboxylic acids…in, or with, water. Green Chemistry 2023, 25 (7) , 2663-2671. https://doi.org/10.1039/D3GC00517H
30. Shuting Dong, Zhijian Zong, Nan Sun, Baoxiang Hu, Zhenlu Shen, Xinquan Hu, Liqun Jin. Hydrosilylative reduction of secondary amides to amines catalyzed by geometry-constrained NNN -cobalt complexes. New Journal of Chemistry 2023, 47 (12) , 5603-5610. https://doi.org/10.1039/D3NJ00372H
31. Zhen-Zhang Weng, Chao-Long Chen, Long-Wu Ye, La-Sheng Long, Lan-Sun Zheng, Xiang-Jian Kong. Lanthanide-oxo clusters for efficient catalytic reduction of carboxamides. Science China Chemistry 2023, 66 (2) , 443-448. https://doi.org/10.1007/s11426-022-1493-y
32. Liana Hie, Tejas K. Shah. Activation of Amide CN Bonds by Nickel Catalysis. 2022, 243-272. https://doi.org/10.1002/9783527830251.ch8
33. Artemiy Nichugovskiy, Varvara Maksimova, Ekaterina Trapeznikova, Elizaveta Eshtukova-Shcheglova, Igor Ivanov, Marianna Yakubovskaya, Kirill Kirsanov, Dmitry Cheshkov, Gian Cesare Tron, Mikhail Maslov. Synthesis of Novel Lipophilic Polyamines via Ugi Reaction and Evaluation of Their Anticancer Activity. Molecules 2022, 27 (19) , 6218. https://doi.org/10.3390/molecules27196218
34. Jinjae Park, Cheol-Hong Cheon. A cyanide-catalyzed imino-Stetter reaction enables the concise total syntheses of rucaparib. RSC Advances 2022, 12 (33) , 21172-21180. https://doi.org/10.1039/D2RA03619C
35. Hao Xu, Ji Ju, Hao Li. Toward efficient heterogeneous catalysts for in-situ hydrodeoxygenation of biomass. Fuel 2022, 320 , 123891. https://doi.org/10.1016/j.fuel.2022.123891
36. H. Keith Chenault. Introduction to Pyrrolidone and Caprolactam Chemistry. 2022, 1-69. https://doi.org/10.1002/9781119468769.hpcbm01
37. Yinbo Liu, Xiaofeng Mo, Irfan Majeed, Mei Zhang, Hui Wang, Zhuo Zeng. An efficient and straightforward approach for accessing thionoesters via palladium-catalyzed C–N cleavage of thioamides. Organic & Biomolecular Chemistry 2022, 20 (7) , 1532-1537. https://doi.org/10.1039/D1OB02349G
38. Artemiy Nichugovskiy, Gian Tron, Mikhail Maslov. Recent Advances in the Synthesis of Polyamine Derivatives and Their Applications. Molecules 2021, 26 (21) , 6579. https://doi.org/10.3390/molecules26216579
39. Laura Köring, Nikolai A. Sitte, Markus Bursch, Stefan Grimme, Jan Paradies. Hydrogenation of Secondary Amides using Phosphane Oxide and Frustrated Lewis Pair Catalysis. Chemistry – A European Journal 2021, 27 (57) , 14179-14183. https://doi.org/10.1002/chem.202100041
40. Zhiqiang Guo, Tengfei Pang, Leilei Yan, Xuehong Wei, Jianbin Chao, Chanjuan Xi. CO 2 -tuned highly selective reduction of formamides to the corresponding methylamines. Green Chemistry 2021, 23 (19) , 7534-7538. https://doi.org/10.1039/D1GC02815D
41. Pragati Pandey, Jitendra K. Bera. Hydrosilylative reduction of primary amides to primary amines catalyzed by a terminal [Ni–OH] complex. Chemical Communications 2021, 57 (73) , 9204-9207. https://doi.org/10.1039/D1CC03537A
42. Morgan Lecomte, Mounsef Lahboubi, Pierre Thilmany, Adil El Bouzakhi, Gwilherm Evano. A general, versatile and divergent synthesis of selectively deuterated amines. Chemical Science 2021, 12 (33) , 11157-11165. https://doi.org/10.1039/D1SC02622D
43. H. Keith Chenault. Introduction to Pyrrolidone and Caprolactam Chemistry. 2021, 1-69. https://doi.org/10.1002/9781119468769.hpcbm001
44. Liang Wang, Yaoyao Wang, Yu Tao, Nana Zhang, Shubai Li. Nickel catalyzed hydrosilane reduction of (het)arenecarboxylic acids into aldehydes. Mendeleev Communications 2021, 31 (2) , 271-273. https://doi.org/10.1016/j.mencom.2021.03.043
45. Christopher C. McAtee, Xu Zhu, Corinna S. Schindler. The synthesis of herqulines B and C. 2021, 247-280. https://doi.org/10.1016/B978-0-12-822212-6.00003-5
46. Olumide Bolarinwa Ayodele. Physicochemical properties of acid/base activated kaolinite modified with oxalic acid-functionalized nickel nanoparticles. Catalysis Today 2020, 358 , 394-402. https://doi.org/10.1016/j.cattod.2019.12.004
47. Sen Li, Kun Jie, Wenjie Yan, Qingjun Pan, Min Zhang, Yufeng Wang, Zhengjiang Fu, Shengmei Guo, Hu Cai. Selective C–C bond cleavage of amides fused to 8-aminoquinoline controlled by a catalyst and an oxidant. Chemical Communications 2020, 56 (89) , 13820-13823. https://doi.org/10.1039/D0CC04960C
48. Emma L. Stoll, Thomas Tongue, Keith G. Andrews, Damien Valette, David J. Hirst, Ross M. Denton. A practical catalytic reductive amination of carboxylic acids. Chemical Science 2020, 11 (35) , 9494-9500. https://doi.org/10.1039/D0SC02271C
49. Jian Zhou, Xiaofan Bo, Li Wan, Zhong Xin. Efficient Reduction of Oxazolyl‐Bearing Secondary Anilides to Amines by Nickel‐Catalyzed Hydrosilylation. Asian Journal of Organic Chemistry 2020, 9 (5) , 818-821. https://doi.org/10.1002/ajoc.202000054
50. Mrinal Bhunia, P Sreejyothi, Swadhin K. Mandal. Earth-abundant metal catalyzed hydrosilylative reduction of various functional groups. Coordination Chemistry Reviews 2020, 405 , 213110. https://doi.org/10.1016/j.ccr.2019.213110
51. Sem Raj Tamang, Arpita Singh, Deepika Bedi, Adineh Rezaei Bazkiaei, Audrey A. Warner, Keeley Glogau, Corey McDonald, Daniel K. Unruh, Michael Findlater. Polynuclear lanthanide–diketonato clusters for the catalytic hydroboration of carboxamides and esters. Nature Catalysis 2020, 3 (2) , 154-162. https://doi.org/10.1038/s41929-019-0405-5
52. Hari S. Das, Shyamal Das, Kartick Dey, Bhagat Singh, Rahul K. Haridasan, Arpan Das, Jasimuddin Ahmed, Swadhin K. Mandal. Primary amides to amines or nitriles: a dual role by a single catalyst. Chemical Communications 2019, 55 (79) , 11868-11871. https://doi.org/10.1039/C9CC05856G
53. Dylan J. Hale, Luke J. Murphy, Robert McDonald, Michael J. Ferguson, Laura Turculet. Hydrosilylative Reduction of Tertiary Amides to Amines Catalyzed by N ‐(Phosphinoaryl)anilido Complexes of Iron and Cobalt. ChemCatChem 2019, 11 (16) , 3818-3827. https://doi.org/10.1002/cctc.201900550
54. Casper M. Macaulay, Takahiko Ogawa, Robert McDonald, Orson L. Sydora, Mark Stradiotto, Laura Turculet. A comparative analysis of hydrosilative amide reduction catalyzed by first-row transition metal (Mn, Fe, Co, and Ni) N -phosphinoamidinate complexes. Dalton Transactions 2019, 48 (26) , 9581-9587. https://doi.org/10.1039/C8DT04221G
55. Jing Li, Martin Berger, Wojciech Zawodny, Marwan Simaan, Nuno Maulide. A Chemoselective α-Oxytriflation Enables the Direct Asymmetric Arylation of Amides. Chem 2019, 5 (7) , 1883-1891. https://doi.org/10.1016/j.chempr.2019.05.006
56. Andrey Khalimon, Kristina Gudun, Davit Hayrapetyan. Base Metal Catalysts for Deoxygenative Reduction of Amides to Amines. Catalysts 2019, 9 (6) , 490. https://doi.org/10.3390/catal9060490
57. Yixiao Pan, Zhenli Luo, Jiahong Han, Xin Xu, Changjun Chen, Haoqiang Zhao, Lijin Xu, Qinghua Fan, Jianliang Xiao. B(C 6 F 5 ) 3 ‐Catalyzed Deoxygenative Reduction of Amides to Amines with Ammonia Borane. Advanced Synthesis & Catalysis 2019, 361 (10) , 2301-2308. https://doi.org/10.1002/adsc.201801447
58. Hyemin Kweon, Sanha Jang, Akerke Bereketova, Ji Chan Park, Kang Hyun Park. Highly dispersed Ni nanoparticles on mesoporous silica nanospheres by melt infiltration for transfer hydrogenation of aryl ketones. RSC Advances 2019, 9 (25) , 14154-14159. https://doi.org/10.1039/C9RA01608B
59. Derek Yiren Ong, Zhihao Yen, Asami Yoshii, Julia Revillo Imbernon, Ryo Takita, Shunsuke Chiba. Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides. Angewandte Chemie 2019, 131 (15) , 5046-5051. https://doi.org/10.1002/ange.201900233
60. Derek Yiren Ong, Zhihao Yen, Asami Yoshii, Julia Revillo Imbernon, Ryo Takita, Shunsuke Chiba. Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides. Angewandte Chemie International Edition 2019, 58 (15) , 4992-4997. https://doi.org/10.1002/anie.201900233
61. Elahe Ghiasbeigi, Mohammad Soleiman‐Beigi. Copper Immobilized on Isonicotinic Acid Hydrazide Functionalized Nano‐Magnetite as a Novel Recyclable Catalyst for Direct Synthesis of Phenols and Anilines. ChemistrySelect 2019, 4 (12) , 3611-3619. https://doi.org/10.1002/slct.201803770
62. Kristina A. Gudun, Medet Segizbayev, Assyl Adamov, Philipp N. Plessow, Konstantin A. Lyssenko, Mannix P. Balanay, Andrey Y. Khalimon. POCN Ni( ii ) pincer complexes: synthesis, characterization and evaluation of catalytic hydrosilylation and hydroboration activities. Dalton Transactions 2019, 48 (5) , 1732-1746. https://doi.org/10.1039/C8DT04854A
63. Alibek Nurseiit, Jaysan Janabel, Kristina A. Gudun, Aishabibi Kassymbek, Medet Segizbayev, Tulegen M. Seilkhanov, Andrey Y. Khalimon. Bench-Stable Cobalt Pre-Catalysts for Mild Hydrosilative Reduction of Tertiary Amides to Amines and Beyond. ChemCatChem 2019, 11 (2) , 790-798. https://doi.org/10.1002/cctc.201801605
64. Ervin Kovács, Balázs Rózsa, Attila Csomos, Imre Csizmadia, Zoltán Mucsi. Amide Activation in Ground and Excited States. Molecules 2018, 23 (11) , 2859. https://doi.org/10.3390/molecules23112859
65. Weijie Guo, Jingjun Huang, Hongxiang Wu, Tingting Liu, Zhongfeng Luo, Junsheng Jian, Zhuo Zeng. One-pot transition-metal free transamidation to sterically hindered amides. Organic Chemistry Frontiers 2018, 5 (20) , 2950-2954. https://doi.org/10.1039/C8QO00591E
66. Michael T. Peruzzi, Qiong Qiong Mei, Stephen J. Lee, Michel R. Gagné. Chemoselective amide reductions by heteroleptic fluoroaryl boron Lewis acids. Chemical Communications 2018, 54 (46) , 5855-5858. https://doi.org/10.1039/C8CC01863D
67. Colin M. Kelly, Robert McDonald, Orson L. Sydora, Mark Stradiotto, Laura Turculet. A Manganese Pre‐Catalyst: Mild Reduction of Amides, Ketones, Aldehydes, and Esters. Angewandte Chemie 2017, 129 (50) , 16117-16120. https://doi.org/10.1002/ange.201709441
68. Colin M. Kelly, Robert McDonald, Orson L. Sydora, Mark Stradiotto, Laura Turculet. A Manganese Pre‐Catalyst: Mild Reduction of Amides, Ketones, Aldehydes, and Esters. Angewandte Chemie International Edition 2017, 56 (50) , 15901-15904. https://doi.org/10.1002/anie.201709441
69. Xiangqian Liu, Huifeng Yue, Jiaqi Jia, Lin Guo, Magnus Rueping. Synthesis of Amidines from Amides Using a Nickel‐Catalyzed Decarbonylative Amination through CO Extrusion Intramolecular Recombination Fragment Coupling. Chemistry – A European Journal 2017, 23 (49) , 11771-11775. https://doi.org/10.1002/chem.201702867