ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Direct Synthesis of Arylketones by Nickel-Catalyzed Addition of Arylboronic Acids to Nitriles

View Author Information
Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan
Cite this: Org. Lett. 2010, 12, 8, 1736–1739
Publication Date (Web):March 24, 2010
https://doi.org/10.1021/ol1003252
Copyright © 2010 American Chemical Society

Article Views

6585

Altmetric

-

Citations

LEARN ABOUT THESE METRICS
Read OnlinePDF (294 KB)
Supporting Info (1)»

Abstract

Abstract Image

A convenient and efficient method for the synthesis of various arylketones by nickel-catalyzed addition of arylboronic acids to nitriles is described. A catalytic cycle involving Ni(II) species as the catalytic intermediates is proposed to account for the present catalytic reaction.

Supporting Information

ARTICLE SECTIONS
Jump To

General experimental procedure and characterization details. This material is available free of charge via the Internet at http://pubs.acs.org.

Terms & Conditions

Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

Cited By

This article is cited by 102 publications.

  1. Philip Boehm, Patrick Müller, Patrick Finkelstein, Miguel A. Rivero-Crespo, Marc-Olivier Ebert, Nils Trapp, Bill Morandi. Mechanistic Investigation of the Nickel-Catalyzed Metathesis between Aryl Thioethers and Aryl Nitriles. Journal of the American Chemical Society 2022, 144 (29) , 13096-13108. https://doi.org/10.1021/jacs.2c01595
  2. Wenwei Li, Honggui Zhou, Yequan He, Ge Zeng, Yumeng Zheng, Yangni Hu, Zhongyan Chen, Jing-Yuan Ge, Ningning Lv, Jiuxi Chen. Synthesis of Diverse γ-Lactams via Rh-Catalyzed C(sp2)–H Addition to Aliphatic Nitriles. Organic Letters 2022, 24 (28) , 5090-5094. https://doi.org/10.1021/acs.orglett.2c01867
  3. Zhenzhu Hu, Yuhang Wang, Peng Ma, Xiaqian Wu, Jianhui Wang. Nickel(0)-Catalyzed Decarbonylative Cross-Coupling of Aromatic Esters with Arylboronic Acids via Chelation Assistance. ACS Omega 2022, 7 (25) , 21537-21545. https://doi.org/10.1021/acsomega.2c01105
  4. Zi-Hao Chen, Rui-Ze Sun, Fei Yao, Xu-Dong Hu, Long-Xue Xiang, Hengjiang Cong, Wen-Bo Liu. Enantioselective Nickel-Catalyzed Reductive Aryl/Alkenyl–Cyano Cyclization Coupling to All-Carbon Quaternary Stereocenters. Journal of the American Chemical Society 2022, 144 (11) , 4776-4782. https://doi.org/10.1021/jacs.2c01237
  5. Xiaoping Hu, Peizhuo Lv, Ninghui Zhang, Yuanhong Liu. Synthesis of ortho-Diamino-Functionalized 1-Arylnaphthalenes through Nickel-Catalyzed Cyclization of Ynamide-Benzylnitriles with Organoboronic Acids. Organic Letters 2021, 23 (20) , 7949-7954. https://doi.org/10.1021/acs.orglett.1c02957
  6. Xuanzeng Ye, Beihang Xu, Jiani Sun, Ling Dai, Yinlin Shao, Yetong Zhang, Jiuxi Chen. Pd-Catalyzed Approach for Assembling 9-Arylacridines via a Cascade Tandem Reaction of 2-(Arylamino)benzonitrile with Arylboronic Acids in Water. The Journal of Organic Chemistry 2020, 85 (20) , 13004-13014. https://doi.org/10.1021/acs.joc.0c01654
  7. Amitava Rakshit, Prashant Kumar, Tipu Alam, Hirendranath Dhara, Bhisma K. Patel. Visible-Light-Accelerated Pd-Catalyzed Cascade Addition/Cyclization of Arylboronic Acids to γ- and β-Ketodinitriles for the Construction of 3-Cyanopyridines and 3-Cyanopyrrole Analogues. The Journal of Organic Chemistry 2020, 85 (19) , 12482-12504. https://doi.org/10.1021/acs.joc.0c01703
  8. L. Reginald Mills, Joshua M. Graham, Purvish Patel, Sophie A. L. Rousseaux. Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation. Journal of the American Chemical Society 2019, 141 (49) , 19257-19262. https://doi.org/10.1021/jacs.9b11208
  9. Tong Xu, Yinlin Shao, Ling Dai, Shulin Yu, Tianxing Cheng, Jiuxi Chen. Pd-Catalyzed Tandem Reaction of 2-Aminostyryl Nitriles with Arylboronic Acids: Synthesis of 2-Arylquinolines. The Journal of Organic Chemistry 2019, 84 (21) , 13604-13614. https://doi.org/10.1021/acs.joc.9b01875
  10. Yunxiang Lei, Wenbo Dai, Yong Tian, Jianhui Yang, Pengfei Li, Jianbing Shi, Bin Tong, Zhengxu Cai, Yuping Dong. Revealing Insight into Long-Lived Room-Temperature Phosphorescence of Host–Guest Systems. The Journal of Physical Chemistry Letters 2019, 10 (20) , 6019-6025. https://doi.org/10.1021/acs.jpclett.9b02411
  11. Xiangmeng Chen, Zicong Chen, Chau Ming So. Exploration of Aryl Phosphates in Palladium-Catalyzed Mono-α-arylation of Aryl and Heteroaryl Ketones. The Journal of Organic Chemistry 2019, 84 (10) , 6337-6346. https://doi.org/10.1021/acs.joc.9b00669
  12. Xicheng Yang, Haihua Yu, Yulong Xu, Liming Shao. Regioselective Access to 3-Aryl-1-aminoisoquinolines via Nickel(I)-Catalyzed C–C and C–N Cascade Coupling Reactions from the Substituted 2-(Cyanomethyl)benzonitriles. The Journal of Organic Chemistry 2018, 83 (17) , 9682-9695. https://doi.org/10.1021/acs.joc.8b01159
  13. Vinoth Kumar Chenniappan, Sajan Silwal, Ronald J. Rahaim. Ni/Ti Dual Catalytic Cross-Coupling of Nitriles and Organobromides To Access Ketones. ACS Catalysis 2018, 8 (5) , 4539-4544. https://doi.org/10.1021/acscatal.8b00244
  14. Mengting Meng, Liangfeng Yang, Kai Cheng, Chenze Qi. Pd(II)-Catalyzed Denitrogenative and Desulfinative Addition of Arylsulfonyl Hydrazides with Nitriles. The Journal of Organic Chemistry 2018, 83 (6) , 3275-3284. https://doi.org/10.1021/acs.joc.8b00211
  15. Tingting Wang, Xiaobi Jing, Chao Chen, and Lei Yu . Organoselenium-Catalyzed Oxidative C═C Bond Cleavage: A Relatively Green Oxidation of Alkenes into Carbonyl Compounds with Hydrogen Peroxide. The Journal of Organic Chemistry 2017, 82 (18) , 9342-9349. https://doi.org/10.1021/acs.joc.7b01245
  16. Yan Yan, Zhiguo Zhang, Yameng Wan, Guisheng Zhang, Nana Ma, and Qingfeng Liu . Hypervalent Iodine(III)-Promoted Phenyl Transfer Reaction from Phenyl Hydrazides to Nitriles. The Journal of Organic Chemistry 2017, 82 (15) , 7957-7963. https://doi.org/10.1021/acs.joc.7b01215
  17. Meijun Xiong, Xin Xie, and Yuanhong Liu . Copper-Catalyzed Borylative Cyclization of in Situ Generated o-Allenylaryl Nitriles with Bis(pinacolato)diboron. Organic Letters 2017, 19 (13) , 3398-3401. https://doi.org/10.1021/acs.orglett.7b01355
  18. Li Shang, Yonghui Chang, Fan Luo, Jia-Ni He, Xin Huang, Lei Zhang, Lichun Kong, Kaixiao Li, and Bo Peng . Redox-Neutral α-Arylation of Alkyl Nitriles with Aryl Sulfoxides: A Rapid Electrophilic Rearrangement. Journal of the American Chemical Society 2017, 139 (11) , 4211-4217. https://doi.org/10.1021/jacs.7b00969
  19. Gaonan Wang, Xu You, Yi Gan, and Yuanhong Liu . Synthesis of δ- and α-Carbolines via Nickel-Catalyzed [2 + 2 + 2] Cycloaddition of Functionalized Alkyne-Nitriles with Alkynes. Organic Letters 2017, 19 (1) , 110-113. https://doi.org/10.1021/acs.orglett.6b03385
  20. Linjun Qi, Kun Hu, Shuling Yu, Jianghe Zhu, Tianxing Cheng, Xiaodong Wang, Jiuxi Chen, and Huayue Wu . Tandem Addition/Cyclization for Access to Isoquinolines and Isoquinolones via Catalytic Carbopalladation of Nitriles. Organic Letters 2017, 19 (1) , 218-221. https://doi.org/10.1021/acs.orglett.6b03499
  21. Wenyan Hao, Haiyi Liu, Lin Yin, and Mingzhong Cai . Phosphine-Free, Heterogeneous Palladium-Catalyzed Atom-Efficient Carbonylative Cross-Coupling of Triarylbismuths with Aryl Iodides: Synthesis of Biaryl Ketones. The Journal of Organic Chemistry 2016, 81 (10) , 4244-4251. https://doi.org/10.1021/acs.joc.6b00570
  22. Hongxiang Wu, Baiping Xu, Yue Li, Fengying Hong, Dezhao Zhu, Junsheng Jian, Xiaoer Pu, and Zhuo Zeng . One-Pot Synthesis of Arylketones from Aromatic Acids via Palladium-Catalyzed Suzuki Coupling. The Journal of Organic Chemistry 2016, 81 (7) , 2987-2992. https://doi.org/10.1021/acs.joc.5b02667
  23. Ya-Chun Hong, Parthasarathy Gandeepan, Subramaniyan Mannathan, Wei-Tse Lee, and Chien-Hong Cheng . Alkene-Assisted Nickel-Catalyzed Regioselective 1,4-Addition of Organoboronic Acid to Dienones: A Direct Route to All-Carbon Quaternary Centers. Organic Letters 2014, 16 (11) , 2806-2809. https://doi.org/10.1021/ol500838h
  24. Guoqin Xia, Xiuling Han, and Xiyan Lu . Pd(II)-Catalyzed One-Step Construction of Cycloalkane-Fused Indoles and Its Application in Formal Synthesis of (±)-Aspidospermidine. Organic Letters 2014, 16 (7) , 2058-2061. https://doi.org/10.1021/ol500662f
  25. Xingyong Wang, Miaochang Liu, Long Xu, Qingzong Wang, Jiuxi Chen, Jinchang Ding, and Huayue Wu . Palladium-Catalyzed Addition of Potassium Aryltrifluoroborates to Aliphatic Nitriles: Synthesis of Alkyl Aryl Ketones, Diketone Compounds, and 2-Arylbenzo[b]furans. The Journal of Organic Chemistry 2013, 78 (11) , 5273-5281. https://doi.org/10.1021/jo400433m
  26. Tao-Shan Jiang and Guan-Wu Wang . Synthesis of 3-Acylindoles by Palladium-Catalyzed Acylation of Free (N–H) Indoles with Nitriles. Organic Letters 2013, 15 (4) , 788-791. https://doi.org/10.1021/ol303440y
  27. Mohamad-Ali Tehfe, Frédéric Dumur, Bernadette Graff, Jean-Louis Clément, Didier Gigmes, Fabrice Morlet-Savary, Jean-Pierre Fouassier, and Jacques Lalevée . New Cleavable Photoinitiator Architecture with Huge Molar Extinction Coefficients for Polymerization in the 340–450 nm Range.. Macromolecules 2013, 46 (3) , 736-746. https://doi.org/10.1021/ma3024359
  28. Fredrik Svensson, Rajendra S. Mane, Jonas Sävmarker, Mats Larhed, and Christian Sköld . Theoretical and Experimental Investigation of Palladium(II)-Catalyzed Decarboxylative Addition of Arenecarboxylic Acid to Nitrile. Organometallics 2013, 32 (2) , 490-497. https://doi.org/10.1021/om3009525
  29. Jen-Chieh Hsieh, Yen-Chung Chen, An-Yi Cheng, and Hsiao-Chun Tseng . Nickel-Catalyzed Intermolecular Insertion of Aryl Iodides to Nitriles: A Novel Method to Synthesize Arylketones. Organic Letters 2012, 14 (5) , 1282-1285. https://doi.org/10.1021/ol300153f
  30. Hu Chen, Zhongbin Huang, Xiaoming Hu, Guo Tang, Pengxiang Xu, Yufen Zhao, and Chien-Hong Cheng . Nickel-Catalyzed Cross-Coupling of Aryl Phosphates with Arylboronic Acids. The Journal of Organic Chemistry 2011, 76 (7) , 2338-2344. https://doi.org/10.1021/jo2000034
  31. Brant Landers, Christophe Berini, Chao Wang, and Oscar Navarro . (N-Heterocyclic Carbene)-Pd-Catalyzed Anaerobic Oxidation of Secondary Alcohols and Domino Oxidation−Arylation Reactions. The Journal of Organic Chemistry 2011, 76 (5) , 1390-1397. https://doi.org/10.1021/jo102385u
  32. Gavin Chit Tsui, Quentin Glenadel, Chan Lau, and Mark Lautens. Rhodium(I)-Catalyzed Addition of Arylboronic Acids to (Benzyl-/Arylsulfonyl)acetonitriles: Efficient Synthesis of (Z)-β-Sulfonylvinylamines and β-Keto Sulfones. Organic Letters 2011, 13 (2) , 208-211. https://doi.org/10.1021/ol102598p
  33. Idris Karakaya, Komal Rizwan, Shahid Munir. Transition‐Metal Catalyzed Coupling Reactions for the Synthesis of (Het)aryl Ketones: An Approach from their Synthesis to Biological Perspectives. ChemistrySelect 2023, 8 (12) https://doi.org/10.1002/slct.202204005
  34. Himanshi Sharma, Manoj Kumar, Aaftaab Sethi, Poonam, Brijesh Rathi. Metal-free construction of aminated isoquinoline frameworks from 2-(2-oxo-2-arylethyl) benzonitrile in an aqueous medium. Green Chemistry 2023, 25 (1) , 167-171. https://doi.org/10.1039/D2GC04044A
  35. Hirendra Nath Dhara, Amitava Rakshit, Tipu Alam, Bhisma K. Patel. Metal-catalyzed reactions of organic nitriles and boronic acids to access diverse functionality. Organic & Biomolecular Chemistry 2022, 20 (21) , 4243-4277. https://doi.org/10.1039/D2OB00288D
  36. Lepeng Chen, Ningning Lv, Qianqian Zhen, Zhongyan Chen, Jingyuan Ge, Jiuxi Chen. Nickel-catalyzed multicomponent reaction of dinitriles and hydrazine hydrochlorides with boronic acids: access to 1,3-diaryl-1 H -pyrazol-5-amines and 4,5-dihydropyridazin-3(2 H )-ones. Organic Chemistry Frontiers 2022, 9 (7) , 1955-1959. https://doi.org/10.1039/D2QO00036A
  37. Sinem Çakır, Serdar Batıkan Kavukcu, Hande Karabıyık, Senthil Rethinam, Hayati Türkmen. C(acyl)–C(sp 2 ) and C(sp 2 )–C(sp 2 ) Suzuki–Miyaura cross-coupling reactions using nitrile-functionalized NHC palladium complexes. RSC Advances 2021, 11 (60) , 37684-37699. https://doi.org/10.1039/D1RA07231E
  38. Chandrasekaran Sivaraj, Thirumanavelan Gandhi. Alternative and Uncommon Acylating Agents – An Alive and Kicking Methodology. Chemistry – An Asian Journal 2021, 16 (19) , 2773-2794. https://doi.org/10.1002/asia.202100691
  39. Abhilash Sharma, Dhiraj Dutta, Pranjal Gogoi. A palladium-catalyzed cascade process for spirooxindole: an alternative way for the synthesis of spiro(indoline-3,2′-quinazolin)-2-ones. Organic & Biomolecular Chemistry 2021, 19 (8) , 1795-1806. https://doi.org/10.1039/D0OB02580A
  40. Ling Dai, Shuling Yu, Yinlin Shao, Renhao Li, Zhongyan Chen, Ningning Lv, Jiuxi Chen. Palladium-catalyzed C–H activation of simple arenes and cascade reaction with nitriles: access to 2,4,5-trisubstituted oxazoles. Chemical Communications 2021, 57 (11) , 1376-1379. https://doi.org/10.1039/D0CC07547G
  41. Jen‐Chieh Hsieh. Transition‐Metal‐Catalyzed Addition/Cyclization Reactions of the C−N Multiple Bonds Containing Species. The Chemical Record 2021, 40 https://doi.org/10.1002/tcr.202100008
  42. Dwaipayan Das, Prasun Mukherjee, Asish R. Das. “On water” palladium catalyzed diastereoselective boronic acid addition to structurally diverse cyclopropane nitriles. Organic & Biomolecular Chemistry 2020, 18 (43) , 8886-8898. https://doi.org/10.1039/D0OB00077A
  43. Shuyi Zhang, Bo Wu, Min Huang, Jingxian Bao, Liangshu Zhong, Yuhan Sun. Tuning of active sites in M/TiO2 for photocatalytic cyanation of olefins with high regioselectivity. Applied Catalysis A: General 2020, 604 , 117787. https://doi.org/10.1016/j.apcata.2020.117787
  44. Ling Dai, Shuling Yu, Wenzhang Xiong, Zhongyan Chen, Tong Xu, Yinlin Shao, Jiuxi Chen. Divergent Palladium‐Catalyzed Tandem Reaction of Cyanomethyl Benzoates with Arylboronic Acids: Synthesis of Oxazoles and Isocoumarins. Advanced Synthesis & Catalysis 2020, 362 (9) , 1893-1898. https://doi.org/10.1002/adsc.202000125
  45. Julin Gong, Kun Hu, Yinlin Shao, Renhao Li, Yetong Zhang, Maolin Hu, Jiuxi Chen. Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles. Organic & Biomolecular Chemistry 2020, 18 (3) , 488-494. https://doi.org/10.1039/C9OB02408E
  46. Qianqian Zhen, Renhao Li, Linjun Qi, Kun Hu, Xinrong Yao, Yinlin Shao, Jiuxi Chen. Nickel( ii )-catalyzed C–C, N–C cascade coupling of ketonitriles into substituted pyrroles and pyridines. Organic Chemistry Frontiers 2020, 7 (2) , 286-291. https://doi.org/10.1039/C9QO01259A
  47. Qianqian Zhen, Lepeng Chen, Linjun Qi, Kun Hu, Yinlin Shao, Renhao Li, Jiuxi Chen. Nickel‐Catalyzed Tandem Reaction of Functionalized Arylacetonitriles with Arylboronic Acids in 2‐MeTHF: Eco‐Friendly Synthesis of Aminoisoquinolines and Isoquinolones. Chemistry – An Asian Journal 2020, 15 (1) , 106-111. https://doi.org/10.1002/asia.201901442
  48. Wen-Peng Mai, Yang Liu, Hong-Dai Sui, Yong-Mei Xiao, Pu Mao, Kui Lu. A Novel Ketonitrile Synthesis by Palladium-Catalyzed Carbonylative Coupling Reactions of Amides with Arylboronic Acids. European Journal of Organic Chemistry 2019, 2019 (48) , 7814-7819. https://doi.org/10.1002/ejoc.201901396
  49. Xinrong Yao, Yinlin Shao, Maolin Hu, Maosheng Zhang, Shaotong Li, Yuanzhi Xia, Tianxing Cheng, Jiuxi Chen. Palladium‐Catalyzed Selective Synthesis of Dibenzo[ c , e ]azepin‐5‐ols and Benzo[ c ]pyrido[2,3‐ e ]azepin‐5‐ols. Advanced Synthesis & Catalysis 2019, 361 (20) , 4707-4713. https://doi.org/10.1002/adsc.201900705
  50. Hao Song, Na Cheng, Li-Qin She, Yi Wu, Wei-Wei Liao. Efficient synthesis of spirooxindolyl oxazol-2(5 H )-ones via palladium( ii )-catalyzed addition of arylboronic acids to nitriles. RSC Advances 2019, 9 (50) , 29424-29428. https://doi.org/10.1039/C9RA07216K
  51. Shengyang Fang, Haihua Yu, Xicheng Yang, Jianqi Li, Liming Shao. Nickel‐Catalyzed Construction of 2,4‐Disubstituted Imidazoles via C–C Coupling and C−N Condensation Cascade Reactions. Advanced Synthesis & Catalysis 2019, 361 (14) , 3312-3317. https://doi.org/10.1002/adsc.201900096
  52. Zhiguo Zhang, Xiang Li, Yinghua Li, Yan Guo, Xunan Zhao, Yan Yan, Kai Sun, Guisheng Zhang. Iodine-mediated aryl transfer reaction from arylhydrazine hydrochlorides to nitriles. Tetrahedron 2019, 75 (26) , 3628-3635. https://doi.org/10.1016/j.tet.2019.05.034
  53. Julin Gong, Kun Hu, Yetong Zhang, Yinlin Shao, Tianxing Cheng, Maolin Hu, Jiuxi Chen. Efficient Tandem Addition/Cyclization for Access to 2,4-Diarylquinazolines via Catalytic Carbopalladation of Nitriles. Molecules 2019, 24 (3) , 463. https://doi.org/10.3390/molecules24030463
  54. Jinwei Yuan, Shuainan Liu, Yongmei Xiao, Pu Mao, Liangru Yang, Lingbo Qu. Palladium-catalyzed oxidative amidation of quinoxalin-2(1 H )-ones with acetonitrile: a highly efficient strategy toward 3-amidated quinoxalin-2(1 H )-ones. Organic & Biomolecular Chemistry 2019, 17 (4) , 876-884. https://doi.org/10.1039/C8OB03061H
  55. Jianghe Zhu, Yinlin Shao, Kun Hu, Linjun Qi, Tianxing Cheng, Jiuxi Chen. Pd-Catalyzed tandem reaction of N -(2-cyanoaryl)benzamides with arylboronic acids: synthesis of quinazolines. Organic & Biomolecular Chemistry 2018, 16 (44) , 8596-8603. https://doi.org/10.1039/C8OB02421A
  56. Dina Moustafa, Chelsea Sweet, Hyun Lim, Brenda Calalpa, Parminder Kaur. Mn/Cu catalyzed addition of arylboronic acid to nitriles: Direct synthesis of arylketones. Tetrahedron Letters 2018, 59 (42) , 3816-3820. https://doi.org/10.1016/j.tetlet.2018.09.021
  57. Yetong Zhang, Yinlin Shao, Julin Gong, Kun Hu, Tianxing Cheng, Jiuxi Chen. Palladium-Catalyzed Tandem Reaction of Quinazolinone-Based Nitriles with Arylboronic Acids: Synthesis of 2-(4-Arylquinazolin-2-yl)anilines. Advanced Synthesis & Catalysis 2018, 360 (17) , 3260-3265. https://doi.org/10.1002/adsc.201800615
  58. Shigeru Sasaki. Sterically crowded triarylphosphines bearing cyano groups. Tetrahedron Letters 2018, 59 (23) , 2251-2255. https://doi.org/10.1016/j.tetlet.2018.04.065
  59. Yogesh Kumar, Yogesh Jaiswal, Amit Kumar. Two-Step One-Pot Synthesis of Unsymmetrical (Hetero)Aryl 1,2-Diketones by Addition-Oxygenation of Potassium Aryltrifluoroborates to (Hetero)Arylacetonitriles. European Journal of Organic Chemistry 2018, 2018 (4) , 494-505. https://doi.org/10.1002/ejoc.201701625
  60. Tao-Shan Jiang, Bei Gan, Xi Wang, Xiuli Zhang. One-pot synthesis of ortho -acylphenols by palladium-catalyzed phenol C–H addition to nitriles. Tetrahedron Letters 2017, 58 (44) , 4197-4199. https://doi.org/10.1016/j.tetlet.2017.09.062
  61. Kai Cheng, Guofang Wang, Mengting Meng, Chenze Qi. Acid-promoted denitrogenative Pd-catalyzed addition of arylhydrazines with nitriles at room temperature. Organic Chemistry Frontiers 2017, 4 (3) , 398-403. https://doi.org/10.1039/C6QO00634E
  62. Haihua Yu, Li Xiao, Xicheng Yang, Liming Shao. Controllable access to multi-substituted imidazoles via palladium( ii )-catalyzed C–C coupling and C–N condensation cascade reactions. Chemical Communications 2017, 53 (70) , 9745-9748. https://doi.org/10.1039/C7CC05315K
  63. Kun Hu, Linjun Qi, Shuling Yu, Tianxing Cheng, Xiaodong Wang, Zhaojun Li, Yuanzhi Xia, Jiuxi Chen, Huayue Wu. Efficient synthesis of isoquinolines in water by a Pd-catalyzed tandem reaction of functionalized alkylnitriles with arylboronic acids. Green Chemistry 2017, 19 (7) , 1740-1750. https://doi.org/10.1039/C7GC00267J
  64. Hongxiang Wu, Yue Li, Ming Cui, Junsheng Jian, Zhuo Zeng. Suzuki Coupling of Amides via Palladium-Catalyzed C-N Cleavage of N -Acylsaccharins. Advanced Synthesis & Catalysis 2016, 358 (23) , 3876-3880. https://doi.org/10.1002/adsc.201600555
  65. Ujwal Pratim Saikia, Farhaz L. Hussain, Mrinaly Suri, Pallab Pahari. Selective N-acetylation of aromatic amines using acetonitrile as acylating agent. Tetrahedron Letters 2016, 57 (10) , 1158-1160. https://doi.org/10.1016/j.tetlet.2016.01.108
  66. Christian A. Malapit, Jonathan T. Reeves, Carl A. Busacca, Amy R. Howell, Chris H. Senanayake. Rhodium-Catalyzed Transnitrilation of Aryl Boronic Acids with Dimethylmalononitrile. Angewandte Chemie 2016, 128 (1) , 334-338. https://doi.org/10.1002/ange.201508122
  67. Christian A. Malapit, Jonathan T. Reeves, Carl A. Busacca, Amy R. Howell, Chris H. Senanayake. Rhodium-Catalyzed Transnitrilation of Aryl Boronic Acids with Dimethylmalononitrile. Angewandte Chemie International Edition 2016, 55 (1) , 326-330. https://doi.org/10.1002/anie.201508122
  68. Hongyun Cai, Likai Xia, Yong Rok Lee. Regioselective construction of diverse and multifunctionalized 2-hydroxybenzophenones for sun protection by indium( iii )-catalyzed benzannulation. Chemical Communications 2016, 52 (49) , 7661-7664. https://doi.org/10.1039/C6CC02381A
  69. Xingjie Zhang, Xin Xie, Yuanhong Liu. Nickel-catalyzed cyclization of alkyne-nitriles with organoboronic acids involving anti-carbometalation of alkynes. Chemical Science 2016, 7 (9) , 5815-5820. https://doi.org/10.1039/C6SC01191H
  70. Wanxiang Zhao, John Montgomery. Functionalization of Styrenes by Copper-Catalyzed Borylation/ ortho -Cyanation and Silver-Catalyzed Annulation Processes. Angewandte Chemie 2015, 127 (43) , 12874-12877. https://doi.org/10.1002/ange.201507303
  71. Wanxiang Zhao, John Montgomery. Functionalization of Styrenes by Copper-Catalyzed Borylation/ ortho -Cyanation and Silver-Catalyzed Annulation Processes. Angewandte Chemie International Edition 2015, 54 (43) , 12683-12686. https://doi.org/10.1002/anie.201507303
  72. Miloslav Semler, Petr Štěpnička. Synthesis of aromatic ketones by Suzuki-Miyaura cross-coupling of acyl chlorides with boronic acids mediated by palladium catalysts deposited over donor-functionalized silica gel. Catalysis Today 2015, 243 , 128-133. https://doi.org/10.1016/j.cattod.2014.06.017
  73. Md Yousuf, Tuluma Das, Susanta Adhikari. Palladium catalyzed decarboxylative acylation of arylboronic acid with ethyl cyanoacetate as a new acylating agent: synthesis of alkyl aryl ketones. New Journal of Chemistry 2015, 39 (11) , 8763-8770. https://doi.org/10.1039/C5NJ01597A
  74. Ya-Min Li, Shi-Sheng Wang, Fuchao Yu, Yuehai Shen, Kwen-Jen Chang. Copper-catalyzed cascade addition/cyclization: highly efficient access to phosphonylated quinoline-2,4(1H,3H)-diones. Organic & Biomolecular Chemistry 2015, 13 (19) , 5376-5380. https://doi.org/10.1039/C5OB00617A
  75. Fangdong Hu, Jinghui Yang, Ying Xia, Chen Ma, Haiping Xia, Yan Zhang, Jianbo Wang. Catalyst-free cross-coupling of N-tosylhydrazones with chromium(0) Fischer carbene complexes: a new approach to diarylethanone. Organic Chemistry Frontiers 2015, 2 (11) , 1450-1456. https://doi.org/10.1039/C5QO00241A
  76. N. Nowrouzi, M. Zarei, F. Roozbin. First direct access to 2-hydroxybenzophenones via nickel-catalyzed cross-coupling of 2-hydroxybenzaldehydes with aryl iodides. RSC Advances 2015, 5 (124) , 102448-102453. https://doi.org/10.1039/C5RA18890C
  77. Tuluma Das, Amarnath Chakraborty, Amitabha Sarkar. Palladium catalyzed addition of arylboronic acid or indole to nitriles: synthesis of aryl ketones. Tetrahedron Letters 2014, 55 (52) , 7198-7202. https://doi.org/10.1016/j.tetlet.2014.11.009
  78. Jiuxi Chen, Jianjun Li, Weike Su. Palladium-Catalyzed Direct Addition of 2-Aminobenzonitriles to Sodium Arylsulfinates: Synthesis of o-Aminobenzophenones. Molecules 2014, 19 (5) , 6439-6449. https://doi.org/10.3390/molecules19056439
  79. Tao-Shan Jiang, Guan-Wu Wang. Synthesis of 2-Acylthiophenes by Palladium-Catalyzed Addition of Thiophenes to Nitriles. Advanced Synthesis & Catalysis 2014, 356 (2-3) , 369-373. https://doi.org/10.1002/adsc.201300843
  80. Jiuxi Chen, Jianjun Li, Weike Su. Palladium-catalyzed tandem reaction of 2-hydroxyarylacetonitriles with sodium sulfinates: one-pot synthesis of 2-arylbenzofurans. Org. Biomol. Chem. 2014, 12 (24) , 4078-4083. https://doi.org/10.1039/C4OB00575A
  81. Jiuxi Chen, Leping Ye, Weike Su. Palladium-catalyzed direct addition of arylboronic acids to 2-aminobenzonitrile derivatives: synthesis, biological evaluation and in silico analysis of 2-aminobenzophenones, 7-benzoyl-2-oxoindolines, and 7-benzoylindoles. Org. Biomol. Chem. 2014, 12 (41) , 8204-8211. https://doi.org/10.1039/C4OB00978A
  82. Rajendra D. Patil, Subbarayappa Adimurthy. Catalytic Methods for Imine Synthesis. Asian Journal of Organic Chemistry 2013, 2 (9) , 726-744. https://doi.org/10.1002/ajoc.201300012
  83. Xingyong Wang, Qingzong Wang, Jiuxi Chen, Miaochang Liu, Jinchang Ding, Huayue Wu. Palladium-Catalysed Addition of Potassium Phenyltrifluoroborate to Dinitriles: Synthesis of Diketone Compounds. Journal of Chemical Research 2013, 37 (8) , 470-472. https://doi.org/10.3184/174751913X13730099043760
  84. Serpil Demir, Murat Yiğit, İsmail Özdemir. Synthesis of rhodium complexes derived from benzimidazolin-2-ylidene ligands and first used for the addition of arylboron to benzonitriles. Journal of Organometallic Chemistry 2013, 732 , 21-26. https://doi.org/10.1016/j.jorganchem.2013.01.025
  85. Tse-Lok Ho, Mary Fieser, Louis Fieser. Nickel Chloride. 2013https://doi.org/10.1002/9780471264194.fos11648.pub2
  86. Tse‐Lok Ho, Mary Fieser, Louis Fieser. Nickel Chloride. 2013, 316-318. https://doi.org/10.1002/9780471264194.fos11648.pub3
  87. Yuanhong Ma, Jingsong You, Feijie Song. Facile Access to 3-Acylindoles through Palladium-Catalyzed Addition of Indoles to Nitriles: The One-Pot Synthesis of Indenoindolones. Chemistry - A European Journal 2013, 19 (4) , 1189-1193. https://doi.org/10.1002/chem.201203354
  88. Min-Hsien Chen, Subramaniyan Mannathan, Pao-Shun Lin, Chien-Hong Cheng. Cobalt(II)-Catalyzed 1,4-Addition of Organoboronic Acids to Activated Alkenes: An Application to Highly cis -Stereoselective Synthesis of Aminoindane Carboxylic Acid Derivatives. Chemistry - A European Journal 2012, 18 (47) , 14918-14922. https://doi.org/10.1002/chem.201202575
  89. Guoqin Xia, Xiuling Han, Xiyan Lu. Palladium(II)-Catalyzed Cyclization Reaction of 2-(Alk-2′-ynyl- oxy)benzonitriles or 2-(Alk-2′-ynylamino)benzonitriles: A Facile Way to 2 H -Chromene and 1,2-Dihydroquinoline Derivatives. Advanced Synthesis & Catalysis 2012, 354 (14-15) , 2701-2705. https://doi.org/10.1002/adsc.201200445
  90. Thomas Meyer Gøgsig. Stoichiometric Studies on the Palladium 1,2-Migration. 2012, 57-70. https://doi.org/10.1007/978-3-642-32099-6_4
  91. Akiko Okamoto, Ryosuke Mitsui, Hideaki Oike, Noriyuki Yonezawa. Lewis Acid-mediated ArS E Aroylation of Naphthalene Derivative: Distinct Second Aroylation Behavior of α-Naphthyl Ketone. Chemistry Letters 2011, 40 (11) , 1283-1284. https://doi.org/10.1246/cl.2011.1283
  92. Florence Collet, Bingrui Song, Felix Rudolphi, Lukas J. Gooßen. Development of Decarboxylative Coupling Processes for the Synthesis of Azomethines and Ketones. European Journal of Organic Chemistry 2011, 2011 (32) , 6486-6501. https://doi.org/10.1002/ejoc.201101103
  93. Guo Tang, Chien-Hong Cheng. Synthesis of α-Hydroxy Carboxylic Acids via a Nickel(II)- Catalyzed Hydrogen Transfer Process. Advanced Synthesis & Catalysis 2011, 353 (11-12) , 1918-1922. https://doi.org/10.1002/adsc.201100241
  94. Jing Liu, Xianya Zhou, Honghua Rao, Fuhong Xiao, Chao-Jun Li, Guo-Jun Deng. Direct Synthesis of Aryl Ketones by Palladium-Catalyzed Desulfinative Addition of Sodium Sulfinates to Nitriles. Chemistry - A European Journal 2011, 17 (29) , 7996-7999. https://doi.org/10.1002/chem.201101252
  95. Honghua Rao, Luo Yang, Qi Shuai, Chao-Jun Li. Rhodium-Catalyzed Aerobic Coupling between Aldehydes and Arenesulfinic Acid Salts: A Novel Synthesis of Aryl Ketones. Advanced Synthesis & Catalysis 2011, 353 (10) , 1701-1706. https://doi.org/10.1002/adsc.201100244
  96. Felix Rudolphi, Bingrui Song, Lukas J. Gooßen. Synthesis of Azomethines from α-Oxocarboxylates, Amines and Aryl Bromides via One-Pot Three-Component Decarboxylative Coupling. Advanced Synthesis & Catalysis 2011, 353 (2-3) , 337-342. https://doi.org/10.1002/adsc.201000798
  97. Pazhamalai Anbarasan, Helfried Neumann, Matthias Beller. A General Rhodium-Catalyzed Cyanation of Aryl and Alkenyl Boronic Acids. Angewandte Chemie 2011, 123 (2) , 539-542. https://doi.org/10.1002/ange.201006044
  98. Pazhamalai Anbarasan, Helfried Neumann, Matthias Beller. A General Rhodium-Catalyzed Cyanation of Aryl and Alkenyl Boronic Acids. Angewandte Chemie International Edition 2011, 50 (2) , 519-522. https://doi.org/10.1002/anie.201006044
  99. Tao Miao, Guan-Wu Wang. Synthesis of ketones by palladium-catalysed desulfitative reaction of arylsulfinic acids with nitriles. Chemical Communications 2011, 47 (33) , 9501. https://doi.org/10.1039/c1cc13352g
  100. Jaganathan Karthikeyan, Kanniyappan Parthasarathy, Chien-Hong Cheng. Synthesis of biarylketones and phthalides from organoboronic acids and aldehydes catalyzed by cobalt complexes. Chemical Communications 2011, 47 (37) , 10461. https://doi.org/10.1039/c1cc13771a
Load all citations

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect