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Journal articles on the topic 'Rh(III)-Catalyzed C-H Activation'

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Author: Grafiati

Published: 6 September 2023

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1

Yang, Xifa, He Wang, Xukai Zhou, and Xingwei Li. "Iridium- and rhodium-catalyzed C–H activation and formyl arylation of benzaldehydes under chelation-assistance." Organic & Biomolecular Chemistry 14, no. 23 (2016): 5233–37. http://dx.doi.org/10.1039/c6ob00825a.

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Mild and efficient synthesis of benzophenones via Ir(iii)- and Rh(iii)-catalyzed, directing group-assisted formyl C–H arylation of benzaldehydes has been achieved using diaryliodonium salts, in which Rh(iii) and Ir(iii) catalysts exhibited a complementary substrate scope.

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2

Luo, Haiqing, Qi Xie, Kai Sun, Jianbo Deng, Lin Xu, Kejun Wang, and Xuzhong Luo. "Rh(iii)-catalyzed C-7 arylation of indolines with arylsilanes via C–H activation." RSC Advances 9, no. 32 (2019): 18191–95. http://dx.doi.org/10.1039/c9ra04142g.

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3

Hu, Hong, Bin-Shi Li, Jing-Lei Xu, Wei Sun, Yong Wang, and Meng Sun. "Rh(iii)-Catalyzed spiroannulation of ketimines with cyclopropenones via sequential C–H/C–C bond activation." Chemical Communications 58, no. 30 (2022): 4743–46. http://dx.doi.org/10.1039/d2cc00421f.

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4

Wang, Qiang, Fang Xie, and Xingwei Li. "Rh(III)-Catalyzed Trifluoromethylthiolation of Indoles via C–H Activation." Journal of Organic Chemistry 80, no. 16 (August 10, 2015): 8361–66. http://dx.doi.org/10.1021/acs.joc.5b00940.

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5

Yang, Wei, Jingyi Wang, He Wang, Lei Li, Yuekai Guan, Xianxiu Xu, and Dayu Yu. "Rhodium(iii)-catalyzed three-component cascade synthesis of 6H-benzo[c]chromenes through C–H activation." Organic & Biomolecular Chemistry 16, no. 38 (2018): 6865–69. http://dx.doi.org/10.1039/c8ob01938j.

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6

Wang, Liang, Wenting Wu, Qun Chen, and Mingyang He. "Rhodium-catalyzed olefination of aryl tetrazoles via direct C–H bond activation." Org. Biomol. Chem. 12, no. 40 (2014): 7923–26. http://dx.doi.org/10.1039/c4ob01440e.

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7

Xie, Peipei, Wei Guo, Dimei Chen, and Yuanzhi Xia. "Multiple pathways for C–H cleavage in cationic Cp*Rh(iii)-catalyzed C–H activation without carboxylate assistance: a computational study." Catalysis Science & Technology 8, no. 16 (2018): 4005–9. http://dx.doi.org/10.1039/c8cy00870a.

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8

Gao, Qian-Ci, Yi-Fei Li, Jun Xuan, and Xiao-Qiang Hu. "Practical synthesis of isocoumarins via Rh(III)-catalyzed C–H activation/annulation cascade." Beilstein Journal of Organic Chemistry 19 (January 30, 2023): 100–106. http://dx.doi.org/10.3762/bjoc.19.10.

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Herein, we report an unprecedented Rh(III)-catalyzed C–H activation/annulation cascade of readily available enaminones with iodonium ylides towards the convenient synthesis of isocoumarins. This coupling system proceeds in useful chemical yields (up to 93%) via a cascade C–H activation, Rh-carbenoid migratory insertion and acid-promoted intramolecular annulation. The success of gram-scale reaction and diverse functionalization of isocoumarins demonstrated the synthetic utility of this protocol.

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9

Cui, Yixin, Dachang Bai, Bingxian Liu, Junbiao Chang, and Xingwei Li. "Rh(iii)-Catalyzed acylation of heteroarenes with cyclobutenones via C–H/C–C bond activation." Chemical Communications 56, no. 100 (2020): 15631–34. http://dx.doi.org/10.1039/d0cc05965j.

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10

Vivek Kumar, Sundaravel, Sundaram Ellairaja, Vanaparthi Satheesh, Vairathevar Sivasamy Vasantha, and Tharmalingam Punniyamurthy. "Rh-Catalyzed regioselective C–H activation and C–C bond formation: synthesis and photophysical studies of indazolo[2,3-a]quinolines." Organic Chemistry Frontiers 5, no. 18 (2018): 2630–35. http://dx.doi.org/10.1039/c8qo00557e.

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11

Hyster, Todd K., Derek M. Dalton, and Tomislav Rovis. "Ligand design for Rh(iii)-catalyzed C–H activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones." Chemical Science 6, no. 1 (2015): 254–58. http://dx.doi.org/10.1039/c4sc02590c.

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12

Wang, Huanan, Shuaiqi Li, Baiquan Wang, and Bin Li. "The regioselective synthesis of 2-phosphinoylindoles via Rh(iii)-catalyzed C–H activation." Organic Chemistry Frontiers 5, no. 1 (2018): 88–91. http://dx.doi.org/10.1039/c7qo00746a.

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13

Xu, Pan, Guoqiang Wang, Zhongkai Wu, Shuhua li, and Chengjian Zhu. "Rh(iii)-catalyzed double C–H activation of aldehyde hydrazones: a route for functionalized 1H-indazole synthesis." Chemical Science 8, no. 2 (2017): 1303–8. http://dx.doi.org/10.1039/c6sc03888c.

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14

He, Shiyu, Xufei Yan, Yanxi Lei, Haifeng Xiang, and Xiangge Zhou. "Rhodium-catalyzed annulative coupling of N-aryl-2-aminopyridine and propargylic amine via selective C–C and C–H bond activation." Chemical Communications 56, no. 15 (2020): 2284–87. http://dx.doi.org/10.1039/c9cc09777e.

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15

Jie, Jiyang, Haoyi Li, Songxiao Wu, Qingyu Chai, Haining Wang, and Xiaobo Yang. "Rh(iii)-catalyzed sequential C–H activation and annulation: access to N-fused heterocycles from arylazoles and α-diazocarbonyl compounds." RSC Advances 7, no. 33 (2017): 20548–52. http://dx.doi.org/10.1039/c7ra03262e.

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16

Tang, Shi-Biao, Xiao-Pan Fu, Gao-Rong Wu, Li-Li Zhang, Ke-Zuan Deng, Jin-Yue Yang, Cheng-Cai Xia, and Ya-Fei Ji. "Rhodium(iii)-catalyzed C4-amidation of indole-oximes with dioxazolones via C–H activation." Organic & Biomolecular Chemistry 18, no. 39 (2020): 7922–31. http://dx.doi.org/10.1039/d0ob01655a.

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17

Peneau, Augustin, Quentin Tricart, Catherine Guillou, and Laurent Chabaud. "Mild rhodium(iii)-catalyzed intramolecular annulation of benzamides with allylic alcohols to access azepinone derivatives." Chemical Communications 54, no. 46 (2018): 5891–94. http://dx.doi.org/10.1039/c8cc03319f.

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18

Yang, Wei, Haonan Zhang, Yu Liu, Cuiman Tang, Xiaohui Xu, and Jiaqi Liu. "Rh(iii)-catalyzed synthesis of dibenzo[b,d]pyran-6-ones from aryl ketone O-acetyl oximes and quinones via C–H activation and C–C bond cleavage." RSC Advances 12, no. 23 (2022): 14435–38. http://dx.doi.org/10.1039/d2ra02074b.

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19

Kim, Yechan, and Sungwoo Hong. "Rh(iii)-catalyzed 7-azaindole synthesis via C–H activation/annulative coupling of aminopyridines with alkynes." Chemical Communications 51, no. 56 (2015): 11202–5. http://dx.doi.org/10.1039/c5cc03497c.

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20

Qi, Zisong, and Xingwei Li. "Rh(III)-catalyzed C–H activation of benzamides: Coupling with quinones." Chinese Journal of Catalysis 36, no. 1 (January 2015): 48–56. http://dx.doi.org/10.1016/s1872-2067(14)60245-x.

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21

Zhang, Qijing, Qianrong Li, and Chengming Wang. "Dual C–H activation: Rh(iii)-catalyzed cascade π-extended annulation of 2-arylindole with benzoquinone." RSC Advances 11, no. 21 (2021): 13030–33. http://dx.doi.org/10.1039/d1ra01779a.

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22

Yu, Bole, Ying Chen, Mei Hong, Pingping Duan, Shifeng Gan, Hui Chao, Zujin Zhao, and Jing Zhao. "Rhodium-catalyzed C–H activation of hydrazines leads to isoquinolones with tunable aggregation-induced emission properties." Chemical Communications 51, no. 76 (2015): 14365–68. http://dx.doi.org/10.1039/c5cc05239d.

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23

Ai, Wen, Yunxiang Wu, Huanyu Tang, Xueyan Yang, Yaxi Yang, Yuanchao Li, and Bing Zhou. "Rh(iii)- or Ir(iii)-catalyzed ynone synthesis from aldehydes via chelation-assisted C–H bond activation." Chemical Communications 51, no. 37 (2015): 7871–74. http://dx.doi.org/10.1039/c5cc00758e.

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A simple and practical synthesis of ynones directly from readily available aldehydes was developed for the first time under mild reaction conditions via a Rh(iii)- or Ir(iii)-catalyzed formyl C–H bond activation.

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24

Lv, Honggui, Jingjing Shi, Junjun Huang, Chao Zhang, and Wei Yi. "Rhodium(iii)-catalyzed and MeOH-involved regioselective mono-alkenylation of N-arylureas with acrylates." Organic & Biomolecular Chemistry 15, no. 34 (2017): 7088–92. http://dx.doi.org/10.1039/c7ob01627a.

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25

Ghosh, Asim Kumar, Sadhanendu Samanta, Payel Ghosh, Sukanya Neogi, and Alakananda Hajra. "Regioselective hydroarylation and arylation of maleimides with indazoles via a Rh(iii)-catalyzed C–H activation." Organic & Biomolecular Chemistry 18, no. 16 (2020): 3093–97. http://dx.doi.org/10.1039/d0ob00353k.

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26

Chen, Renjie, Jifeng Qi, Zhenjun Mao, and Sunliang Cui. "Rh(iii)-catalyzed C–H activation/cyclization of oximes with alkenes for regioselective synthesis of isoquinolines." Organic & Biomolecular Chemistry 14, no. 26 (2016): 6201–4. http://dx.doi.org/10.1039/c6ob00942e.

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27

Zhang, Fangming, Xin Zhu, Bo Luo, and Chengming Wang. "Rh(iii)-catalyzed regioselective C–H activation dialkenylation/annulation cascade for rapid access to 6H-isoindolo[2,1-a]indole." RSC Advances 11, no. 41 (2021): 25194–98. http://dx.doi.org/10.1039/d1ra02998c.

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28

Jadhav, Sandip B., Sundaram Maurya, N. Navaneetha, and Rambabu Chegondi. "Rh(iii)-catalyzed diastereoselective cascade annulation of enone-tethered cyclohexadienones via C(sp²)–H bond activation." Chemical Communications 57, no. 99 (2021): 13598–601. http://dx.doi.org/10.1039/d1cc05941f.

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29

Liao, Gang, Hong Song, Xue-Song Yin, and Bing-Feng Shi. "Expeditious synthesis of pyrano[2,3,4-de]quinolines via Rh(iii)-catalyzed cascade C–H activation/annulation/lactonization of quinolin-4-ol with alkynes." Chemical Communications 53, no. 55 (2017): 7824–27. http://dx.doi.org/10.1039/c7cc04113f.

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30

Xie, Hui, Jia-Lin Song, Chun-Yong Jiang, Yan-Xia Huang, Jun-Yi Zeng, Xu-Ge Liu, Shang-Shi Zhang, and Fan Yang. "Thioether-directed Rh(iii)-catalyzed peri-selective acyloxylation of arenes." Organic & Biomolecular Chemistry 20, no. 3 (2022): 565–69. http://dx.doi.org/10.1039/d1ob02236a.

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31

Kondalarao, Koneti, Somratan Sau, and Akhila K. Sahoo. "Sulfoximine Assisted C–H Activation and Annulation via Vinylene Transfer: Access to Unsubstituted Benzothiazines." Molecules 28, no. 13 (June 27, 2023): 5014. http://dx.doi.org/10.3390/molecules28135014.

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In this study, we report the synthesis of unsubstituted 1,2-benzothiazines through a redox-neutral Rh(III)-catalyzed C–H activation and [4+2]-annulation of S–aryl sulfoximines with vinylene carbonate. Notably, the introduction of an N-protected amino acid ligand significantly enhances the reaction rate. The key aspect of this redox-neutral process is the utilization of vinylene carbonate as an oxidizing acetylene surrogate and an efficient vinylene transfer agent. This vinylene carbonate enables the cyclization with the sulfoximine motifs, successfully forming a diverse array of 1,2-benzothiazine derivatives in moderate to good yields. Importantly, this study highlights the potential of Rh(III)-catalyzed C–H activation and [4+2]-annulation reactions for the synthesis of optically pure 1,2-benzothiazines with high enantiomeric purity.

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32

Sun, Peng, Youzhi Wu, Yue Huang, Xiaoming Wu, Jinyi Xu, Hequan Yao, and Aijun Lin. "Rh(iii)-catalyzed redox-neutral annulation of azo and diazo compounds: one-step access to cinnolines." Organic Chemistry Frontiers 3, no. 1 (2016): 91–95. http://dx.doi.org/10.1039/c5qo00331h.

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33

Wang, Run, Xiong Xie, Hong Liu, and Yu Zhou. "Rh(III)-Catalyzed C–H Bond Activation for the Construction of Heterocycles with sp3-Carbon Centers." Catalysts 9, no. 10 (September 30, 2019): 823. http://dx.doi.org/10.3390/catal9100823.

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Rh(III)-catalyzed C–H activation features mild reaction conditions, good functional group tolerance, high reaction efficiency, and regioselectivity. Recently, it has attracted tremendous attention and has been employed to synthesize various heterocycles, such as indoles, isoquinolines, isoquinolones, pyrroles, pyridines, and polyheterocycles, which are important privileged structures in biological molecules, natural products, and agrochemicals. In this short review, we attempt to present an overview of recent advances in Rh(III)-mediated C–H bond activation to generate diverse heterocyclic scaffolds with sp3 carbon centers.

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34

Zheng, Guangfan, Miaomiao Tian, Youwei Xu, Xiaohong Chen, and Xingwei Li. "Rhodium(iii)-catalyzed annulative coupling between arenes and sulfoxonium ylides via C–H activation." Organic Chemistry Frontiers 5, no. 6 (2018): 998–1002. http://dx.doi.org/10.1039/c7qo01033h.

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35

Qi, Zisong, Guo-Dong Tang, Cheng-Ling Pan, and Xingwei Li. "Rhodium(iii)-catalyzed annulation of arenes with alkynes assisted by an internal oxidizing N–O bond." Organic & Biomolecular Chemistry 13, no. 45 (2015): 10977–80. http://dx.doi.org/10.1039/c5ob01886b.

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36

Zhang, Linghua, Yuanshuang Xu, Xiaopeng Zhang, Xinying Zhang, and Xuesen Fan. "Synthesis of pyrazolone fused benzodiazepines via Rh(iii)-catalyzed [4 + 3] annulation of 1-phenylpyrazolidinones with propargyl alcohols." Organic Chemistry Frontiers 7, no. 16 (2020): 2284–90. http://dx.doi.org/10.1039/d0qo00657b.

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An efficient synthesis of pyrazolone fused benzodiazepines through an unprecedented regioselective [4 + 3] annulation of 1-phenylpyrazolidinones with propargyl alcohols via Rh(iii)-catalyzed redox-neutral C–H/N–H/C–O bond activation is presented.

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37

Lv, Honggui, Jingjing Shi, Bo Wu, Yujuan Guo, Junjun Huang, and Wei Yi. "One-pot synthesis of 2,3-difunctionalized indoles via Rh(iii)-catalyzed carbenoid insertion C–H activation/cyclization." Organic & Biomolecular Chemistry 15, no. 38 (2017): 8054–58. http://dx.doi.org/10.1039/c7ob01977g.

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38

Li, Xiang, Ruihong Zhang, Yaoting Qi, Qing Zhao, and Tuanli Yao. "Rhodium(iii)-catalyzed C–H activation/annulation of N-iminopyridinium ylides with alkynes and diazo compounds." Organic Chemistry Frontiers 8, no. 6 (2021): 1190–96. http://dx.doi.org/10.1039/d0qo01333a.

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39

Chen, Lu, Zhichao Wang, Yangyang Wang, Liqiang Hao, Xiaobo Xu, Gaorong Wu, and Yafei Ji. "Rhodium(iii)-catalyzed cascade C–H functionalization/annulation of sulfoximines with iodonium ylides for the synthesis of cyclohexanone-1,2-benzothiazines." Organic & Biomolecular Chemistry 20, no. 4 (2022): 887–94. http://dx.doi.org/10.1039/d1ob02110a.

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40

Kong, De-Shen, Yi-Fan Wang, Yun-Xuan Tan, Jun-Li Zhang, Jian-Ge Zhang, Ping Tian, and Guo-Qiang Lin. "Trisannulation of benzamides and cyclohexadienone-tethered 1,1-disubstituted allenes initiated by Cp*Rh(iii)-catalyzed C–H activation." Organic Chemistry Frontiers 6, no. 5 (2019): 699–703. http://dx.doi.org/10.1039/c8qo01279b.

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41

Yao, Jiayi, Lingheng Kong, and Xingwei Li. "Rhodium-catalyzed coupling of arenes and fluorinated α-diazo diketones: synthesis of chromones." Chemical Communications 56, no. 86 (2020): 13169–72. http://dx.doi.org/10.1039/d0cc05664b.

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42

Ding, Qiuping, Tong Liu, Qiang Zheng, Yadong Zhang, Ling Long, and Yiyuan Peng. "Rh(iii)-catalyzed tandem oxidative olefination-cyclization of aryl sulfonamides." RSC Adv. 4, no. 93 (2014): 51309–14. http://dx.doi.org/10.1039/c4ra09041a.

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An efficient Rh(iii)-catalyzed ortho-selective C–H activation and tandem oxidative olefination-cyclization of aryl sulfonamides is described. The protocol has been applied to various substrates with good functional group tolerance.

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43

Shi, Jingjing, Jie Zhou, Yunnan Yan, Jinlong Jia, Xuelei Liu, Huacan Song, H. Eric Xu, and Wei Yi. "One-pot cascade synthesis of N-methoxyisoquinolinediones via Rh(iii)-catalyzed carbenoid insertion C–H activation/cyclization." Chemical Communications 51, no. 4 (2015): 668–71. http://dx.doi.org/10.1039/c4cc08407a.

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44

Li, Chao, Hui-Bei Xu, Jing Zhang, Man Liu, and Lin Dong. "Synthesis of rhodium(iii)-catalyzed isoquinoline derivatives from allyl carbonates and benzimidates with hydrogen evolution." Organic & Biomolecular Chemistry 18, no. 7 (2020): 1412–16. http://dx.doi.org/10.1039/c9ob02553g.

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A novel Rh(iii)-catalyzed cascade C–H activation/cyclization approach to access isoquinoline derivatives from benzimidates and available allyl carbonates with the liberation of H₂ has been realized.

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45

Jia, Jinlong, Jingjing Shi, Jie Zhou, Xuelei Liu, Yanling Song, H. Eric Xu, and Wei Yi. "Rhodium(iii)-catalyzed C–H activation and intermolecular annulation with terminal alkynes: from indoles to carbazoles." Chemical Communications 51, no. 14 (2015): 2925–28. http://dx.doi.org/10.1039/c4cc09823d.

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46

Wu, Weirong, Yuxia Liu, and Siwei Bi. "Mechanistic insight into conjugated N–N bond cleavage by Rh(iii)-catalyzed redox-neutral C–H activation of pyrazolones." Organic & Biomolecular Chemistry 13, no. 30 (2015): 8251–60. http://dx.doi.org/10.1039/c5ob00977d.

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47

Senthilkumar, Natarajan, Parthasarathy Gandeepan, Jayachandran Jayakumar, and Chien-Hong Cheng. "Rh(iii)-catalyzed synthesis of 1-substituted isoquinolinium salts via a C–H bond activation reaction of ketimines with alkynes." Chem. Commun. 50, no. 23 (2014): 3106–8. http://dx.doi.org/10.1039/c3cc49467e.

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48

Chen, Dianpeng, Gangdong Xing, and Hongwei Zhou. "Sulfone promoted Rh(iii)-catalyzed C–H activation and base assisted 1,5-H shift strategy for the construction of seven-membered rings." Organic Chemistry Frontiers 2, no. 8 (2015): 947–50. http://dx.doi.org/10.1039/c5qo00089k.

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49

Liang, Yujie, Ke Yu, Bin Li, Shansheng Xu, Haibin Song, and Baiquan Wang. "Rh(iii)-catalyzed synthesis of 1-aminoindole derivatives from 2-acetyl-1-arylhydrazines and diazo compounds in water." Chem. Commun. 50, no. 46 (2014): 6130–33. http://dx.doi.org/10.1039/c4cc01520g.

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50

Liu, Yanfei, Jiaping Wu, Baiyang Qian, and Yongjia Shang. "Controllable construction of isoquinolinedione and isocoumarin scaffolds via RhIII-catalyzed C–H annulation of N-tosylbenzamides with diazo compounds." Organic & Biomolecular Chemistry 17, no. 38 (2019): 8768–77. http://dx.doi.org/10.1039/c9ob01789e.

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