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Journal articles on the topic 'Au alkynes hydroarylation'

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Author: Grafiati

Published: 25 May 2024

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1

Duan, Chang-Lin, Xing-Yu Liu, Yun-Xuan Tan, Rui Ding, Shiping Yang, Ping Tian, and Guo-Qiang Lin. "Acetic Acid-Promoted Rhodium(III)-Catalyzed Hydroarylation of Terminal Alkynes." Synlett 30, no. 08 (March 26, 2019): 932–38. http://dx.doi.org/10.1055/s-0037-1611780.

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Rhodium(III)-catalyzed hydroarylation of terminal alkynes has not previously been achieved because of the inevitable oligomerization and other side reactions. Here, we report a novel Cp*Rh(III)-catalyzed hydroarylation of terminal alkynes in acetic acid as solvent to facilitate the C–H bond activation and subsequent transformations. This reaction proceeds under mild conditions, providing an effective approach to the synthesis of alkenylated heterocycles in high to excellent yields (31–99%) with a broad substrate scope (37 examples) and good functional-group compatibility. In this transformation, the loading of the alkyne can be reduced to 1.2 equivalents, which indicates the significant role of HOAc in lowering the reaction temperature and suppressing the oligomerization of the terminal alkyne. Preliminary mechanistic studies are also presented.

2

Tubaro, Cristina, Marco Baron, Andrea Biffis, and Marino Basato. "Alkyne hydroarylation with Au N-heterocyclic carbene catalysts." Beilstein Journal of Organic Chemistry 9 (February 5, 2013): 246–53. http://dx.doi.org/10.3762/bjoc.9.29.

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Mono- and dinuclear gold complexes with N-heterocyclic carbene (NHC) ligands have been employed as catalysts in the intermolecular hydroarylation of alkynes with simple unfunctionalised arenes. Both mono- and dinuclear gold(III) complexes were able to catalyze the reaction; however, the best results were obtained with the mononuclear gold(I) complex IPrAuCl. This complex, activated with one equivalent of silver tetrafluoroborate, exhibited under acidic conditions at room temperature much higher catalytic activity and selectivity compared to more commonly employed palladium(II) catalysts. Moreover, the complex was active, albeit to a minor extent, even under neutral conditions, and exhibited lower activity but higher selectivity compared to the previously published complex AuCl(PPh3). Preliminary results on intramolecular hydroarylations using this catalytic system indicate, however, that alkyne hydration by traces of water may become a serious competing reaction.

3

Zhang, Chaofeng, Songkui Lv, Yanru Wang, Jingyi Zhang, Xiao-Na Wang, and Junbiao Chang. "Metal-free intramolecular hydroarylation of alkynes." Organic Chemistry Frontiers 9, no. 5 (2022): 1300–1307. http://dx.doi.org/10.1039/d1qo01831k.

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An efficient metal-free intramolecular hydroarylation reaction of alkynes is described here. A series of aryl and N-group attached alkynes generated the intramolecular hydroarylation products in high yields.

4

Zhao, JiaKai, Qi Mou, RuiHan Niu, RuYuan Zhao, and Bo Sun. "Environmentally Friendly Cp*Co(III)-catalyzed C-H Bond Hydroarylation of Alkynes." Journal of Physics: Conference Series 2076, no. 1 (November 1, 2021): 012038. http://dx.doi.org/10.1088/1742-6596/2076/1/012038.

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Abstract A facile synthetic method of Alkenylarene derivatives via cobalt(III)-catalyzed C-H hydroarylation with terminal alkynes has been presented. This helpful protocol provides a way to use terminal alkynes to couple with aryl groups through 1, 2-insertion, with high yield and good selectivity to obtain the corresponding hydroarylation products.

5

de Mendoza, Paula, and Antonio M. Echavarren. "Synthesis of arenes and heteroarenes by hydroarylation reactions catalyzed by electrophilic metal complexes." Pure and Applied Chemistry 82, no. 4 (March 10, 2010): 801–20. http://dx.doi.org/10.1351/pac-con-09-10-06.

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The hydroarylation of alkynes (also known as arylation of alkynes or alkenylation of arenes) catalyzed by gold or other electrophilic metal salts or complexes is reviewed from synthetic and mechanistic perspectives.

6

Thowfik, Salam, C. M. A. Afsina, and Gopinathan Anilkumar. "Ruthenium-catalyzed hydroarylation reactions as the strategy towards the synthesis of alkylated arenes and substituted alkenes." RSC Advances 13, no. 9 (2023): 6246–63. http://dx.doi.org/10.1039/d3ra00211j.

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Metal catalyzed hydroarylation reactions achieve C–C or C-heteroatom bonds in an atom economical and step economical manner. Here we cover the literature from 2016 to 2022 to summarize the recent advancements in Ru-catalyzed hydroarylation reactions of alkenes and alkynes.

7

Panda, Niranjan, Irshad Mattan, Subhadra Ojha, and Chandra Shekhar Purohit. "Synthesis of medium-sized (6–7–6) ring compounds by iron-catalyzed dehydrogenative C–H activation/annulation." Organic & Biomolecular Chemistry 16, no. 42 (2018): 7861–70. http://dx.doi.org/10.1039/c8ob01496e.

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8

Luo, Cuicui, Hongwei Yang, Rongfang Mao, Chunxu Lu, and Guangbin Cheng. "An efficient Au(i) catalyst for double hydroarylation of alkynes with heteroarenes." New Journal of Chemistry 39, no. 5 (2015): 3417–23. http://dx.doi.org/10.1039/c4nj02170c.

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9

Yamamoto, Y., E. Ohkubo, and M. Shibuya. "Selective synthesis of trisubstituted (trifluoromethyl)alkenes via ligand-free Cu-catalyzed syn hydroarylation, hydroalkenylation and hydroallylation of (trifluoromethyl)alkynes." Green Chemistry 18, no. 17 (2016): 4628–32. http://dx.doi.org/10.1039/c6gc01782g.

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10

Chen, Bin, Yan Jiang, Jiang Cheng, and Jin-Tao Yu. "Rhodium-catalyzed hydroarylation of alkynes via tetrazole-directed C–H activation." Organic & Biomolecular Chemistry 13, no. 10 (2015): 2901–4. http://dx.doi.org/10.1039/c5ob00064e.

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11

Reetz, Manfred T., and Knut Sommer. "Gold-Catalyzed Hydroarylation of Alkynes." European Journal of Organic Chemistry 2003, no. 18 (September 2003): 3485–96. http://dx.doi.org/10.1002/ejoc.200300260.

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12

LaFortune, James H. W., Julia M. Bayne, Timothy C. Johnstone, Louie Fan, and Douglas W. Stephan. "Catalytic double hydroarylation of alkynes to 9,9-disubstituted 9,10-dihydroacridine derivatives by an electrophilic phenoxyphosphonium dication." Chemical Communications 53, no. 100 (2017): 13312–15. http://dx.doi.org/10.1039/c7cc08037a.

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13

Padala, Kishor, and Masilamani Jeganmohan. "Ruthenium-catalyzed highly regio- and stereoselective hydroarylation of aromatic sulfoxides with alkynes via C–H bond activation." Chem. Commun. 50, no. 93 (2014): 14573–76. http://dx.doi.org/10.1039/c4cc06426g.

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14

Takahashi, Ikko, Takeshi Fujita, Noriaki Shoji, and Junji Ichikawa. "Brønsted acid-catalysed hydroarylation of unactivated alkynes in a fluoroalcohol–hydrocarbon biphasic system: construction of phenanthrene frameworks." Chemical Communications 55, no. 63 (2019): 9267–70. http://dx.doi.org/10.1039/c9cc04152d.

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15

Hu, Feng, and Michal Szostak. "Ruthenium(0)-catalyzed hydroarylation of alkynes via ketone-directed C–H functionalization using in situ-generated ruthenium complexes." Chemical Communications 52, no. 62 (2016): 9715–18. http://dx.doi.org/10.1039/c6cc04537e.

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16

Echavarren, Antonio M., and Cristina Nevado. "Transition Metal-Catalyzed Hydroarylation of Alkynes." Synthesis 2005, no. 02 (2005): 167–82. http://dx.doi.org/10.1055/s-2005-861781.

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17

Campagne, Jean-Marc, Christophe Dal Zotto, Johny Wehbe, and David Virieux. "FeCl3-Catalyzed Intramolecular Hydroarylation of Alkynes." Synlett 2008, no. 13 (July 15, 2008): 2033–35. http://dx.doi.org/10.1055/s-2008-1077954.

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18

Wang, Yun-Long, Wen-Man Zhang, Jian-Jun Dai, Yi-Si Feng, and Hua-Jian Xu. "Cu-catalyzed intramolecular hydroarylation of alkynes." RSC Adv. 4, no. 106 (November 11, 2014): 61706–10. http://dx.doi.org/10.1039/c4ra12258e.

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19

Nakao, Yoshiaki. "Hydroarylation of alkynes catalyzed by nickel." Chemical Record 11, no. 5 (September 6, 2011): 242–51. http://dx.doi.org/10.1002/tcr.201100023.

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20

de Mendoza, Paula, and Antonio M. Echavarren. "ChemInform Abstract: Intramolecular Hydroarylation of Alkynes." ChemInform 44, no. 1 (January 1, 2013): no. http://dx.doi.org/10.1002/chin.201301177.

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21

Manikandan, Rajendran, and Masilamani Jeganmohan. "Recent advances in the ruthenium-catalyzed hydroarylation of alkynes with aromatics: synthesis of trisubstituted alkenes." Organic & Biomolecular Chemistry 13, no. 42 (2015): 10420–36. http://dx.doi.org/10.1039/c5ob01472g.

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The hydroarylation of alkynes with amide, azole, carbamate, phosphine oxide, amine, acetyl, sulfoxide and sulphur substituted aromatics in the presence of a ruthenium catalyst via chelation-assisted C–H bond activation is discussed.

22

Qian, Zhen-Chao, Jun Zhou, Bo Li, Fang Hu, and Bing-Feng Shi. "Rh(iii)-catalyzed regioselective hydroarylation of alkynes via directed C–H functionalization of pyridines." Org. Biomol. Chem. 12, no. 22 (2014): 3594–97. http://dx.doi.org/10.1039/c4ob00612g.

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Rh(iii)-catalyzed C-3 selective alkenylation of pyridines via hydroarylation of alkynes has been developed. The reaction shows high regioselectivity, high yield and good functional group tolerance, providing a convenient strategy for the synthesis of trisubstituted alkenes.

23

Shibuya, Tetsuro, Kyosuke Nakamura, and Ken Tanaka. "Cationic gold(I) axially chiral biaryl bisphosphine complex-catalyzed atropselective synthesis of heterobiaryls." Beilstein Journal of Organic Chemistry 7 (July 6, 2011): 944–50. http://dx.doi.org/10.3762/bjoc.7.105.

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It has been established that a cationic gold(I)/(R)-DTBM-Segphos or (R)-BINAP complex catalyzes the atropselective intramolecular hydroarylation of alkynes leading to enantioenriched axially chiral 4-aryl-2-quinolinones and 4-arylcoumarins with up to 61% ee.

24

Gu, Guangxin, Hao Guo, Yang Li, Yu Wang, Dawen Xu, and Ruiwen Jin. "AlCl3-Catalyzed Intramolecular Hydroarylation of Arenes with Alkynes." Synlett 28, no. 16 (July 6, 2017): 2159–62. http://dx.doi.org/10.1055/s-0036-1588479.

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Herein, we wish to report the main-group metal Lewis acid catalyzed intramolecular hydroarylation of arenes with alkynes. This cyclization proceeds efficiently in the presence of a catalytic amount of AlCl3, affording phenanthrenes in moderate to excellent yields. The catalyst is cheap and nontoxic. The functional-group tolerance is high. A plausible electrophilic aromatic substitution reaction mechanism is proposed for this transformation.

25

Xie, Jin, Zhongfei Yan, and Chengjian Zhu. "Manganese(I)-Catalyzed Selective Functionalization of Alkynes." Synlett 30, no. 02 (November 30, 2018): 124–28. http://dx.doi.org/10.1055/s-0037-1610335.

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Mn(I)-catalyzed selective functionalization of alkynes permits the convenient synthesis of substituted alkenes with high step and atom economies. Although the insertion of five-membered chelated manganacycle intermediates into alkynes has been widely reported, nonchelated Ar–Mn(I) species originating from commercially available arylboronic acids are unprecedented. Our new protocol achieved a challenging hydroarylation of unsymmetrical 1,3-diynes with arylboronic acids with complete regio-, stereo-, and chemoselectivity to give a wide array of trisubstituted conjugated (Z)-enynes in moderate to good yields.

26

Schipper, Derek J., Marieke Hutchinson, and Keith Fagnou. "Rhodium(III)-Catalyzed Intermolecular Hydroarylation of Alkynes." Journal of the American Chemical Society 132, no. 20 (May 26, 2010): 6910–11. http://dx.doi.org/10.1021/ja103080d.

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27

Xu, Dawen, Ramon Rios, Feifei Ba, Dongmei Ma, Guangxin Gu, Aishun Ding, Yunyan Kuang, and Hao Guo. "Photoinduced Intramolecular Haloarylation and Hydroarylation of Alkynes." Asian Journal of Organic Chemistry 5, no. 8 (June 17, 2016): 981–85. http://dx.doi.org/10.1002/ajoc.201600232.

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28

Godoi, Marla N., Francisco de Azambuja, Pablo David G. Martinez, Nelson H. Morgon, Vanessa G. Santos, Thaís Regiani, Denis Lesage, et al. "Revisiting the Intermolecular Fujiwara Hydroarylation of Alkynes." European Journal of Organic Chemistry 2017, no. 13 (April 3, 2017): 1794–803. http://dx.doi.org/10.1002/ejoc.201700033.

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29

Guo, Jing, Odelia Cheong, Karlee L. Bamford, Jiliang Zhou, and Douglas W. Stephan. "Frustrated Lewis pair-catalyzed double hydroarylation of alkynes with N-substituted pyrroles." Chemical Communications 56, no. 12 (2020): 1855–58. http://dx.doi.org/10.1039/c9cc08654d.

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Metal-free hydroarylation of alkynes with N-substituted pyrroles is shown to be efficiently mediated by B(C₆F₅)₃ to yield variants of dipyrrole methanes. The mechanism is shown to proceed via an FLP addition pathway.

30

Fujiwara, Yuzo, and Chengguo Jia. "New developments in transition metal-catalyzed synthetic reactions via C-H bond activation." Pure and Applied Chemistry 73, no. 2 (January 1, 2001): 319–24. http://dx.doi.org/10.1351/pac200173020319.

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Several novel and useful reactions involving transition metal-catalyzed C-H bond activation discovered in our laboratory have been summarized here, which includes olefin arylation, hydroarylation of alkynes, carboxylation of arenes and alkanes, and acetoxylation and aminomethylation of alkanes. Possible mechanisms of these reactions have been suggested.

31

Pascual, Sergio, Christophe Bour, Paula de Mendoza, and Antonio M. Echavarren. "Synthesis of fluoranthenes by hydroarylation of alkynes catalyzed by gold(I) or gallium trichloride." Beilstein Journal of Organic Chemistry 7 (November 14, 2011): 1520–25. http://dx.doi.org/10.3762/bjoc.7.178.

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Electrophilic gold(I) catalyst 6 competes with GaCl3 as the catalyst of choice in the synthesis of fluoranthenes by intramolecular hydroarylation of alkynes. The potential of this catalyst for the preparation of polyarenes is illustrated by a synthesis of two functionalized decacyclenes in a one-pot transformation in which three C–C bonds are formed with high efficiency.

32

Cacchi, Sandro, Giancarlo Fabrizi, Antonella Goggiamani, and Daniela Persiani. "Palladium-Catalyzed Hydroarylation of Alkynes with Arenediazonium Salts." Organic Letters 10, no. 8 (April 2008): 1597–600. http://dx.doi.org/10.1021/ol800266e.

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33

Xu, Xiaoling, Jiuxi Chen, Wenxia Gao, Huayue Wu, Jinchang Ding, and Weike Su. "Palladium-catalyzed hydroarylation of alkynes with arylboronic acids." Tetrahedron 66, no. 13 (March 2010): 2433–38. http://dx.doi.org/10.1016/j.tet.2010.01.086.

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34

Zhang, Jing, Ruja Shrestha, John F. Hartwig, and Pinjing Zhao. "A decarboxylative approach for regioselective hydroarylation of alkynes." Nature Chemistry 8, no. 12 (September 5, 2016): 1144–51. http://dx.doi.org/10.1038/nchem.2602.

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35

Nakao, Yoshiaki. "ChemInform Abstract: Hydroarylation of Alkynes Catalyzed by Nickel." ChemInform 43, no. 7 (January 23, 2012): no. http://dx.doi.org/10.1002/chin.201207268.

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36

Wang, Yun-Long, Wen-Man Zhang, Jian-Jun Dai, Yi-Si Feng, and Hua-Jian Xu. "ChemInform Abstract: Cu-Catalyzed Intramolecular Hydroarylation of Alkynes." ChemInform 46, no. 19 (April 23, 2015): no. http://dx.doi.org/10.1002/chin.201519041.

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37

Wang, Xulun, Lihong Zhou, and Wenjun Lu. "Hydroarylation of Alkynes via Aryl C-H Bond Cleavage." Current Organic Chemistry 14, no. 3 (February 1, 2010): 289–307. http://dx.doi.org/10.2174/138527210790231964.

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38

Hahn, Christine, Mayra Miranda, Nagendra P. B. Chittineni, Trent A. Pinion, and Ricardo Perez. "Mechanistic Studies on Platinum(II) Catalyzed Hydroarylation of Alkynes." Organometallics 33, no. 12 (June 11, 2014): 3040–50. http://dx.doi.org/10.1021/om5003123.

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39

Bhaskar, G., C. Saikumar, and P. T. Perumal. "Indium(III) bromide-catalyzed hydroarylation of alkynes with indoles." Tetrahedron Letters 51, no. 23 (June 2010): 3141–45. http://dx.doi.org/10.1016/j.tetlet.2010.04.036.

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40

Liu, Saiwen, Yang Bai, Xiangxiang Cao, Fuhong Xiao, and Guo-Jun Deng. "Palladium-catalyzed desulfitative hydroarylation of alkynes with sodium sulfinates." Chemical Communications 49, no. 68 (2013): 7501. http://dx.doi.org/10.1039/c3cc43723j.

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41

Hanna, Luke E., Mikhail O. Konev, and Elizabeth R. Jarvo. "Nickel-Catalyzed Directed Hydroarylation of Alkynes with Boronic Acids." European Journal of Organic Chemistry 2019, no. 1 (November 25, 2018): 184–87. http://dx.doi.org/10.1002/ejoc.201801494.

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42

Schipper, Derek J., Marieke Hutchinson, and Keith Fagnou. "ChemInform Abstract: Rhodium(III)-Catalyzed Intermolecular Hydroarylation of Alkynes." ChemInform 41, no. 36 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.201036116.

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43

Mehrabi, Tahmineh, and Alireza Ariafard. "The different roles of a cationic gold(i) complex in catalysing hydroarylation of alkynes and alkenes with a heterocycle." Chemical Communications 52, no. 60 (2016): 9422–25. http://dx.doi.org/10.1039/c6cc04370d.

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44

Yamamoto, Yoshihiko. "Synthesis of heterocycles via transition-metal-catalyzed hydroarylation of alkynes." Chem. Soc. Rev. 43, no. 5 (2014): 1575–600. http://dx.doi.org/10.1039/c3cs60369e.

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45

Lin, Baoda, Miaochang Liu, Zhishi Ye, Qin Zhang, and Jiang Cheng. "Rhodium–copper–TBAF-catalyzed hydroarylation of alkynes with aryl Trimethoxysilanes." Tetrahedron Letters 50, no. 15 (April 2009): 1714–16. http://dx.doi.org/10.1016/j.tetlet.2009.01.130.

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46

Nagamoto, Midori, Jun-ichi Fukuda, Miyuki Hatano, Hideki Yorimitsu, and Takahiro Nishimura. "Hydroxoiridium-Catalyzed Hydroarylation of Alkynes and Bicycloalkenes with N-Sulfonylbenzamides." Organic Letters 19, no. 21 (October 19, 2017): 5952–55. http://dx.doi.org/10.1021/acs.orglett.7b02950.

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47

Yoshikai, N., K. Gao, P. S. Lee, and T. Fujita. "Cobalt-Catalyzed Hydroarylation of Alkynes Through C-H Bond Activation." Synfacts 2010, no. 12 (November 22, 2010): 1410. http://dx.doi.org/10.1055/s-0030-1258858.

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48

Xu, Xiaoling, Jiuxi Chen, Wenxia Gao, Huayue Wu, Jinchang Ding, and Weike Su. "ChemInform Abstract: Palladium-Catalyzed Hydroarylation of Alkynes with Arylboronic Acids." ChemInform 41, no. 33 (July 24, 2010): no. http://dx.doi.org/10.1002/chin.201033043.

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49

Shaikh, Aslam C., S. Shalini, Ramanathan Vaidhyanathan, Manoj V. Mane, Ayan Kumar Barui, Chitta Ranjan Patra, Yeduru Venkatesh, Prakriti Ranjan Bangal, and Nitin T. Patil. "Identifying Solid Luminogens through Gold-Catalysed Intramolecular Hydroarylation of Alkynes." European Journal of Organic Chemistry 2015, no. 22 (June 30, 2015): 4860–67. http://dx.doi.org/10.1002/ejoc.201500503.

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50

Borsini, Elena, Gianluigi Broggini, Andrea Fasana, Chiara Baldassarri, Angelo M. Manzo, and Alcide D. Perboni. "Access to pyrrolo-pyridines by gold-catalyzed hydroarylation of pyrroles tethered to terminal alkynes." Beilstein Journal of Organic Chemistry 7 (October 26, 2011): 1468–74. http://dx.doi.org/10.3762/bjoc.7.170.

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In a simple procedure, the intramolecular hydroarylation of N-propargyl-pyrrole-2-carboxamides was accomplished with the aid of gold(III) catalysis. The reaction led to differently substituted pyrrolo[2,3-c]pyridine and pyrrolo[3,2-c]pyridine derivatives arising either from direct cyclization or from a formal rearrangement of the carboxamide group. Terminal alkynes are essential to achieve bicyclic pyrrolo-fused pyridinones by a 6-exo-dig process, while the presence of a phenyl group at the C–C triple bond promotes the 7-endo-dig cyclization giving pyrrolo-azepines.