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Enantioselective Synthesis of 3,4-Dihydroisoquinolin-1(2H)-ones by Nickel-Catalyzed Denitrogenative Annulation of 1,2,3-Benzotriazin-4(3H)-ones with Allenes

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    Enantioselective Synthesis of 3,4-Dihydroisoquinolin-1(2H)-ones by Nickel-Catalyzed Denitrogenative Annulation of 1,2,3-Benzotriazin-4(3H)-ones with Allenes
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    Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2010, 132, 1, 54–55
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    https://doi.org/10.1021/ja909603j
    Published December 15, 2009
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    Abstract

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    A denitrogenative annulation reaction of 1,2,3-benzotriazin-4(3H)-ones with allenes catalyzed by a nickel−phosphine complex to produce a variety of substituted 3,4-dihydroisoquinolin-1(2H)-ones in a regioselective manner is described. A highly enantioselective version, as well as structural evidence for the mechanistic course of this reaction, is also presented.

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    Experimental procedures, spectral data for the new compounds, and details of the X-ray analysis of Ni(II) complex 2 (CIF). This material is available free of charge via the Internet at http://pubs.acs.org.

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    31. Zhiqi He and Yong Huang . Diverting C–H Annulation Pathways: Nickel-Catalyzed Dehydrogenative Homologation of Aromatic Amides. ACS Catalysis 2016, 6 (11) , 7814-7823. https://doi.org/10.1021/acscatal.6b02477
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    36. Hao Wang and Shouyun Yu . Synthesis of Isoquinolones Using Visible-Light-Promoted Denitrogenative Alkyne Insertion of 1,2,3-Benzotriazinones. Organic Letters 2015, 17 (17) , 4272-4275. https://doi.org/10.1021/acs.orglett.5b01960
    37. Zhong Xing, Fang Huang, Chuanzhi Sun, Xue Zhao, Jianbiao Liu, and Dezhan Chen . Density Functional Theory Study of Rh(III)-Catalyzed C–H Activations and Intermolecular Annulations between Benzamide Derivatives and Allenes. Inorganic Chemistry 2015, 54 (8) , 3958-3969. https://doi.org/10.1021/acs.inorgchem.5b00134
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    39. Qiuzheng Tang, Dexin Xia, Xiqing Jin, Qing Zhang, Xiao-Qiang Sun, and Congyang Wang . Re/Mg Bimetallic Tandem Catalysis for [4+2] Annulation of Benzamides and Alkynes via C-H/N-H Functionalization. Journal of the American Chemical Society 2013, 135 (12) , 4628-4631. https://doi.org/10.1021/ja400020e
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    42. Tomoya Miura, Tsuneaki Biyajima, Tetsuji Fujii, and Masahiro Murakami . Synthesis of α-Amino Ketones from Terminal Alkynes via Rhodium-Catalyzed Denitrogenative Hydration of N-Sulfonyl-1,2,3-triazoles. Journal of the American Chemical Society 2012, 134 (1) , 194-196. https://doi.org/10.1021/ja2104203
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    44. Tomoya Miura, Yui Nishida, Masao Morimoto, Motoshi Yamauchi, and Masahiro Murakami . Palladium-Catalyzed Denitrogenation Reaction of 1,2,3-Benzotriazin-4(3H)-ones Incorporating Isocyanides. Organic Letters 2011, 13 (6) , 1429-1431. https://doi.org/10.1021/ol103143a
    45. Yosuke Ochi, Takuya Kurahashi, and Seijiro Matsubara . Decarbonylative Cycloaddition of Phthalic Anhydrides with Allenes. Organic Letters 2011, 13 (6) , 1374-1377. https://doi.org/10.1021/ol200044y
    46. Nobuyoshi Maizuru, Tasuku Inami, Takuya Kurahashi, and Seijiro Matsubara . Nickel-Catalyzed Cycloaddition of Anthranilic Acid Derivatives to Alkynes. Organic Letters 2011, 13 (5) , 1206-1209. https://doi.org/10.1021/ol200090g
    47. Tomoya Miura, Masao Morimoto, and Masahiro Murakami. Enantioselective [2 + 2 + 2] Cycloaddition Reaction of Isocyanates and Allenes Catalyzed by Nickel. Journal of the American Chemical Society 2010, 132 (45) , 15836-15838. https://doi.org/10.1021/ja105541r
    48. Kyohei Fujiwara, Takuya Kurahashi, and Seijiro Matsubara. Decarbonylative Cycloaddition of Phthalimides with 1,3-Dienes. Organic Letters 2010, 12 (20) , 4548-4551. https://doi.org/10.1021/ol101842y
    49. Tomoya Miura, Masao Morimoto, Motoshi Yamauchi and Masahiro Murakami. Nickel-Catalyzed Denitrogenative Annulation Reactions of 1,2,3-Benzotriazin-4(3H)-ones with 1,3-Dienes and Alkenes. The Journal of Organic Chemistry 2010, 75 (15) , 5359-5362. https://doi.org/10.1021/jo1008756
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    56. Kanagaraj Madasamy. Recent Advances in Denitrogenative Organic Transformations of 1,2,3‐Benzotriazin‐4(3 H )‐ones. Asian Journal of Organic Chemistry 2024, 13 (7) https://doi.org/10.1002/ajoc.202400127
    57. Fang‐Bei Ge, Chuan‐Jun Lu, Xiao Chen, Wang Yao, Mei An, Yu‐Kun Jiang, Li‐Ping Xu, Ren‐Rong Liu. Enantioselective Nickel‐Catalyzed Denitrogenative Transannulation En Route to N−N Atropisomers. Angewandte Chemie 2024, 136 (26) https://doi.org/10.1002/ange.202400441
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    72. Rochelle McGrory, Réka J. Faggyas, Andrew Sutherland. One-pot synthesis of N -substituted benzannulated triazoles via stable arene diazonium salts. Organic & Biomolecular Chemistry 2021, 19 (27) , 6127-6140. https://doi.org/10.1039/D1OB00968K
    73. Tianlei Li, Jishun Li, Zihao Zhu, Yuyuan Chen, Xueyao Li, Qingyun Yang, Jie Xia, Wenxuan Zhang, Chao Zhang, Weidong Pan, Song Wu. Metallaphotoredox-catalyzed C–H activation: regio-selective annulation of allenes with benzamide. Organic Chemistry Frontiers 2021, 8 (5) , 928-935. https://doi.org/10.1039/D0QO01127D
    74. Fushan Chen, Shanshan Hu, Sipei Li, Guo Tang, Yufen Zhao. Visible-light-induced denitrogenative phosphorylation of benzotriazinones: a metal- and additive-free method for accessing ortho -phosphorylated benzamide derivatives. Green Chemistry 2021, 23 (1) , 296-301. https://doi.org/10.1039/D0GC03613G
    75. Chen Chen, Liying Liu, Wan Sun, Jie Ding, Yan-Ping Zhu, Bolin Zhu. Pd/NBE-catalyzed sequential carbamoylation/olefination of aryl iodides. Organic Chemistry Frontiers 2020, 7 (20) , 3179-3185. https://doi.org/10.1039/D0QO00905A
    76. Michael M. Yamano, Andrew V. Kelleghan, Qianzhen Shao, Maude Giroud, Bryan J. Simmons, Bo Li, Shuming Chen, K. N. Houk, Neil K. Garg. Intercepting fleeting cyclic allenes with asymmetric nickel catalysis. Nature 2020, 586 (7828) , 242-247. https://doi.org/10.1038/s41586-020-2701-2
    77. Mahesh R. Kulkarni, Nitin D. Gaikwad. Recent Advances in Synthesis of 3,4‐Dihydroisoquinolin‐1(2 H )‐one. ChemistrySelect 2020, 5 (27) , 8157-8184. https://doi.org/10.1002/slct.202002131
    78. N. Brosy. denitrogenative transannulation. 2020https://doi.org/10.1002/9783527809080.cataz04996
    79. Zhenhua Wang, Xiu Wang, Yasushi Nishihara. Nickel or Palladium‐Catalyzed Decarbonylative Transformations of Carboxylic Acid Derivatives. Chemistry – An Asian Journal 2020, 15 (8) , 1234-1247. https://doi.org/10.1002/asia.202000117
    80. Guanlin Li, Xiaohong Huo, Xieyang Jiang, Wanbin Zhang. Asymmetric synthesis of allylic compounds via hydrofunctionalisation and difunctionalisation of dienes, allenes, and alkynes. Chemical Society Reviews 2020, 49 (7) , 2060-2118. https://doi.org/10.1039/C9CS00400A
    81. Changduo Pan, Chao Wu, Cheng Yuan, Jin-Tao Yu. Cascade arylchloromethylation of unactivated alkenes for the construction of chloromethyl substituted dihydroisoquinolinones. Tetrahedron Letters 2020, 61 (7) , 151499. https://doi.org/10.1016/j.tetlet.2019.151499
    82. Yiting Li, Song Sun, Jiang Cheng, Jin-Tao Yu. Alkylarylation of N -allylbenzamides and N -allylanilines with simple ethers for the direct construction of ether substituted dihydroisoquinolinones and indolines. Organic & Biomolecular Chemistry 2020, 18 (4) , 650-654. https://doi.org/10.1039/C9OB02565K
    83. Jie Ren, Xinxin Yan, Xiaofan Cui, Chao Pi, Yangjie Wu, Xiuling Cui. Iodine-catalysed N-centered [1,2]-rearrangement of 3-aminoindazoles with anilines: efficient access to 1,2,3-benzotriazines. Green Chemistry 2020, 22 (1) , 265-269. https://doi.org/10.1039/C9GC03567B
    84. Shigeru Arai, Arisa Izaki, Yuka Amako, Masaya Nakajima, Masanobu Uchiyama, Atsushi Nishida. Regioselective [2+2+2] Cycloaddition Reaction Using Allene‐ynes with Simple Allenes under Nickel Catalysis. Advanced Synthesis & Catalysis 2019, 361 (21) , 4882-4887. https://doi.org/10.1002/adsc.201900719
    85. . Enantioselective Nickel‐Catalyzed Domino Reactions. 2019, 213-247. https://doi.org/10.1002/9783527822539.ch6
    86. Xiao‐Ceng Liu, Kai Sun, Xiao‐Lan Chen, Wen‐Fei Wang, Yan Liu, Qian‐Li Li, Yu‐Yu Peng, Ling‐Bo Qu, Bing Yu. Visible‐Light‐Promoted Transition‐Metal‐Free Approach toward Phosphoryl‐Substituted Dihydroisoquinolones via Cascade Phosphorylation/Cyclization of N ‐Allylbenzamides. Advanced Synthesis & Catalysis 2019, 361 (16) , 3712-3717. https://doi.org/10.1002/adsc.201900544
    87. Pei‐Chao Zhang, Jie Han, Junliang Zhang. Pd/PC‐Phos‐Catalyzed Enantioselective Intermolecular Denitrogenative Cyclization of Benzotriazoles with Allenes and N‐Allenamides. Angewandte Chemie International Edition 2019, 58 (33) , 11444-11448. https://doi.org/10.1002/anie.201904805
    88. Pei‐Chao Zhang, Jie Han, Junliang Zhang. Pd/PC‐Phos‐Catalyzed Enantioselective Intermolecular Denitrogenative Cyclization of Benzotriazoles with Allenes and N‐Allenamides. Angewandte Chemie 2019, 131 (33) , 11566-11570. https://doi.org/10.1002/ange.201904805
    89. Navjeet Kaur. Nickel catalysis: six membered heterocycle syntheses. Synthetic Communications 2019, 49 (9) , 1103-1133. https://doi.org/10.1080/00397911.2019.1568499
    90. Yang Liu, Marco Bandini. Nickel Catalyzed Functionalization of Allenes. Chinese Journal of Chemistry 2019, 37 (5) , 431-441. https://doi.org/10.1002/cjoc.201800568
    91. Dinesh S. Barak, Sushobhan Mukhopadhyay, Dipak J. Dahatonde, Sanjay Batra. NaNO2/I2 as an alternative reagent for the synthesis of 1,2,3-benzotriazin-4(3H)-ones from 2-aminobenzamides. Tetrahedron Letters 2019, 60 (3) , 248-251. https://doi.org/10.1016/j.tetlet.2018.12.025
    92. Vijaykumar H. Thorat, Nitinkumar Satyadev Upadhyay, Chien‐Hong Cheng. Nickel‐Catalyzed Denitrogenative ortho ‐Arylation of Benzotriazinones with Organic Boronic Acids: an Efficient Route to Losartan and Irbesartan Drug Molecules. Advanced Synthesis & Catalysis 2018, 360 (24) , 4784-4789. https://doi.org/10.1002/adsc.201800923
    93. Chen-Guang Li, Guo-Qiang Xu, Peng-Fei Xu. Synthesis of quinazolinone derivatives via a visible-light photocatalyzed denitrogenation rearrangement process. Journal of Photochemistry and Photobiology A: Chemistry 2018, 355 , 25-31. https://doi.org/10.1016/j.jphotochem.2017.12.004
    94. Vijaykumar H. Thorat, Nitinkumar Satyadev Upadhyay, Masahiro Murakami, Chien‐Hong Cheng. Nickel‐Catalyzed Denitrogenative Annulation of 1,2,3‐Benzotriazin‐4‐(3 H )‐ones with Benzynes for Construction of Phenanthridinone Scaffolds. Advanced Synthesis & Catalysis 2018, 360 (2) , 284-289. https://doi.org/10.1002/adsc.201701143
    95. Daniel Solé, Israel Fernández. Controlling Selectivities in Palladium-Catalyzed Cyclization Reactions Leading to Heterocycles. 2018, 311-337. https://doi.org/10.1016/B978-0-12-811651-7.00008-X
    96. Amrita Mondal, Priyanka Kundu, Moumita Jash, Chinmay Chowdhury. Palladium-catalysed stereoselective synthesis of 4-(diarylmethylidene)-3,4-dihydroisoquinolin-1(2 H )-ones: expedient access to 4-substituted isoquinolin-1(2 H )-ones and isoquinolines. Organic & Biomolecular Chemistry 2018, 16 (6) , 963-980. https://doi.org/10.1039/C7OB02788E
    97. Xia Yao, Lu Jin, Yu Rao. Synthesis of Phosphaisoquinolin‐1‐one by Annulation of Aryl Phosphinamides with Allenes through a Cobalt‐Promoted C−H Functionalization. Asian Journal of Organic Chemistry 2017, 6 (7) , 825-830. https://doi.org/10.1002/ajoc.201700215
    98. Tse‐Lok Ho, Mary Fieser, Louis Fieser. Chiral Auxiliaries and Catalysts. 2017https://doi.org/10.1002/9780471264194.fos02343.pub6
    99. Ramadoss Boobalan, Ramajayam Kuppusamy, Rajagopal Santhoshkumar, Parthasarathy Gandeepan, Chien‐Hong Cheng. Access to Isoquinolin‐1(2  H )‐ones and Pyridones by Cobalt‐Catalyzed Oxidative Annulation of Amides with Allenes. ChemCatChem 2017, 9 (2) , 273-277. https://doi.org/10.1002/cctc.201601190
    100. Tianlei Li, Chao Zhang, Yonghua Tan, Weidong Pan, Yu Rao. Cobalt-catalyzed C–H activation and regioselective intermolecular annulation with allenes. Organic Chemistry Frontiers 2017, 4 (2) , 204-209. https://doi.org/10.1039/C6QO00567E
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    Cite this: J. Am. Chem. Soc. 2010, 132, 1, 54–55
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