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Journal articles on the topic 'Palladium-catalyzed arylation'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Dodonova, Jelena, and Sigitas Tumkevicius. "Fused Pyrrolo[2,3-d]pyrimidines (7-Deazapurines) by Palladium-Catalyzed Direct N–H and C–H Arylation Reactions." Synthesis 49, no. 11 (2017): 2523–34. http://dx.doi.org/10.1055/s-0036-1588734.

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Palladium-catalyzed intramolecular direct C–H arylations for the synthesis of hitherto unknown fused hetero systems containing an incorporated pyrrolo[2,3-d]pyrimidine scaffold are described. Pyrimido[5′,4′:4,5]pyrrolo[2,1-a]isoindoles were synthesized from 2,4-diarylpyrrolo[2,3-d]pyrimidines and o-bromobenzyl bromides by using a cascade N-benzylation/C–H arylation reaction sequence. A series of pyrimido[5′,4′:4,5]pyrrolo[1,2-f]phenanthridines were successfully assembled via a domino process involving the palladium-catalyzed direct double C–H arylation reactions of 2,4,7-triarylpyrrolo[2,3-d]

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2

Abdelmalek, Fatiha, Fazia Derridj, Safia Djebbar, Jean-François Soulé та Henri Doucet. "Efficient synthesis of π-conjugated molecules incorporating fluorinated phenylene units through palladium-catalyzed iterative C(sp2)–H bond arylations". Beilstein Journal of Organic Chemistry 11 (28 жовтня 2015): 2012–20. http://dx.doi.org/10.3762/bjoc.11.218.

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We report herein a two or three step synthesis of fluorinated π-conjugated oligomers through iterative C–H bond arylations. Palladium-catalyzed desulfitative arylation of heteroarenes allowed in a first step the synthesis of fluoroaryl-heteroarene units in high yields. Then, the next steps involve direct arylation with aryl bromides catalyzed by PdCl(C3H5)(dppb) to afford triad or tetrad heteroaromatic compounds via regioselective activation of C(sp2)–H bonds.

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3

Maiti, Debabrata, Sumon Basak, and Jyoti Prasad Biswas. "Transition-Metal-Catalyzed C–H Arylation Using Organoboron Reagents." Synthesis 53, no. 18 (2021): 3151–79. http://dx.doi.org/10.1055/a-1485-4666.

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AbstractAryl rings are ubiquitous in the core of numerous natural product and industrially important molecules and thus their facile synthesis is of major interest in the scientific community and industry. Although multiple strategies enable access to these skeletons, metal-catalyzed C–H activation is promising due to its remarkable efficiency. Commercially available organoboron reagents, a prominent arylating partner in the cross-coupling domain, have also been utilized for direct arylation. Organoborons are bench-stable, inexpensive, and readily available coupling partners that promise regio

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4

Huang, Qing, Liangxian Liu, Jiayi Zhu, Yu Chen, Feng Lin, and Baoshuang Wang. "Highly Regioselective Arylation of 1,2,3-Triazole N-Oxides with Sodium Arenesulfinates via Palladium-Catalyzed Desulfitative Cross-Coupling Reaction." Synlett 26, no. 08 (2015): 1124–30. http://dx.doi.org/10.1055/s-0034-1380186.

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A convenient and highly regioselective palladium-catalyzed direct C5-arylation of 1,2,3-triazole N-oxides was developed in the presence of silver carbonate and tripotassium phosphate. This protocol allowed use of sodium arylsulfinates, diphenylphosphine oxide, and triphenylphosphine as arylating reagents to produce 2-aryl-5-aryl-1,2,3-triazole N-oxides in good to excellent yields, providing a complement to the existing methods for the direct arylation of 1,2,3-triazole N-oxides.

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5

Della Ca’, Nicola. "Palladium-Catalyzed Reactions." Catalysts 11, no. 5 (2021): 588. http://dx.doi.org/10.3390/catal11050588.

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Palladium is probably the most versatile and exploited transition metal in catalysis due to its capability to promote a myriad of organic transformations both at laboratory and industrial scales (alkylation, arylation, cyclization, hydrogenation, oxidation, isomerization, cross-coupling, cascade, radical reactions, etc [...]

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6

Peng, Jing, Chao Chen та Chanjuan Xi. "β-Arylation of oxime ethers using diaryliodonium salts through activation of inert C(sp)–H bonds using a palladium catalyst". Chem. Sci. 7, № 2 (2016): 1383–87. http://dx.doi.org/10.1039/c5sc03903g.

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7

Christodoulou, Michael S., Egle M. Beccalli, and Sabrina Giofrè. "Palladium-Catalyzed Benzodiazepines Synthesis." Catalysts 10, no. 6 (2020): 634. http://dx.doi.org/10.3390/catal10060634.

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This review is focused on palladium-catalyzed reactions as efficient strategies aimed at the synthesis of different classes of benzodiazepines. Several reaction typologies are reported including hydroamination, amination, C–H arylation, N-arylation, and the Buchwald–Hartwig reaction, depending on the different substrates identified as halogenated starting materials (activated substrates) or unactivated unsaturated systems, which then exploit Pd(0)- or Pd(II)-catalytic species. In particular, the use of the domino reactions, as intra- or intermolecular processes, are reported as an efficient an

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8

Du, Zhengyin, Hua Feng, Fangli Gang, Yang Che, and Ying Fu. "Palladium-Catalyzed Regioselective C-5 Arylation of 1,2,3-Triazoles with Diaryliodonium Salts." Synlett 28, no. 13 (2017): 1624–29. http://dx.doi.org/10.1055/s-0036-1588815.

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An effective method for C-5 arylation of 1,4-disubstituted 1,2,3-triazoles and C-5 regioselective arylation of 1-substituted 1,2,3-triazoles via sp2 C–H activation with palladium as a catalyst and diaryliodonium salts as arylating reagents is described. Various electron-rich and electron-deficient substituents attached to triazoles and diaryliodonium salts were tolerable to give the desired products with good isolated yields in 24 hours under air atmosphere.

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9

Liu, Ren-Rong, Teng-Fei Xu, Yong-Gang Wang, Bin Xiang, Jian-Rong Gao, and Yi-Xia Jia. "Palladium-catalyzed dearomative arylalkynylation of indoles." Chemical Communications 52, no. 94 (2016): 13664–67. http://dx.doi.org/10.1039/c6cc06262h.

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10

Dyker, Gerald, Stefan Borowski, Gerald Henkel, Andreas Kellner, Ina Dix, and Peter G. Jones. "Palladium-catalyzed arylation of butadiynes." Tetrahedron Letters 41, no. 43 (2000): 8259–62. http://dx.doi.org/10.1016/s0040-4039(00)01474-x.

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11

Brusoe, Andrew T., and John F. Hartwig. "Palladium-Catalyzed Arylation of Fluoroalkylamines." Journal of the American Chemical Society 137, no. 26 (2015): 8460–68. http://dx.doi.org/10.1021/jacs.5b02512.

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12

Mitin, A. V., A. N. Kashin, and I. P. Beletskaya. "Palladium-Catalyzed Arylation of Sulfones." Russian Journal of Organic Chemistry 40, no. 6 (2004): 802–12. http://dx.doi.org/10.1023/b:rujo.0000044542.70121.04.

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13

Dyker, Gerald, Jörg Heiermann, Masahiro Miura, et al. "Palladium-Catalyzed Arylation of Cyclopentadienes." Chemistry - A European Journal 6, no. 18 (2000): 3426–33. http://dx.doi.org/10.1002/1521-3765(20000915)6:18<3426::aid-chem3426>3.0.co;2-b.

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14

Stolley, Ryan M., Wenxing Guo, and Janis Louie. "Palladium-Catalyzed Arylation of Cyanamides." Organic Letters 14, no. 1 (2011): 322–25. http://dx.doi.org/10.1021/ol203069p.

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15

Canterbury, Daniel P., Kevin D. Hesp та Jana Polivkova. "Palladium-catalyzed β-(hetero)arylation of α,β-unsaturated valerolactams". Organic & Biomolecular Chemistry 14, № 32 (2016): 7731–34. http://dx.doi.org/10.1039/c6ob01126h.

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16

Long, Rongrong, Xufei Yan, Zhiqing Wu, Zhengkai Li, Haifeng Xiang, and Xiangge Zhou. "Palladium-catalyzed direct arylation of phenols with aryl iodides." Organic & Biomolecular Chemistry 13, no. 12 (2015): 3571–74. http://dx.doi.org/10.1039/c5ob00132c.

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17

Oeser, Petr, Jakub Koudelka, Artem Petrenko, and Tomáš Tobrman. "Recent Progress Concerning the N-Arylation of Indoles." Molecules 26, no. 16 (2021): 5079. http://dx.doi.org/10.3390/molecules26165079.

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This review summarizes the current state-of-the-art procedures in terms of the preparation of N-arylindoles. After a short introduction, the transition-metal-free procedures available for the N-arylation of indoles are briefly discussed. Then, the nickel-catalyzed and palladium-catalyzed N-arylation of indoles are both discussed. In the next section, copper-catalyzed procedures for the N-arylation of indoles are described. The final section focuses on recent findings in the field of biologically active N-arylindoles.

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18

Chen, Kai, Xin Li, Shuo-Qing Zhang та Bing-Feng Shi. "Palladium-catalyzed C(sp3)–H arylation of lactic acid: efficient synthesis of chiral β-aryl-α-hydroxy acids". Organic Chemistry Frontiers 3, № 2 (2016): 204–8. http://dx.doi.org/10.1039/c5qo00319a.

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19

Liu, Ren-Rong, Yang Xu, Ren-Xiao Liang, et al. "Spirooxindole synthesis via palladium-catalyzed dearomative reductive-Heck reaction." Organic & Biomolecular Chemistry 15, no. 13 (2017): 2711–15. http://dx.doi.org/10.1039/c7ob00146k.

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20

Cao, Ke, Yawen Huang, Junxiao Yang, and Ji Wu. "Palladium catalyzed selective mono-arylation of o-carboranes via B–H activation." Chemical Communications 51, no. 33 (2015): 7257–60. http://dx.doi.org/10.1039/c5cc01331c.

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21

Zhang, Xiao-Wen, Hui Zhang, Hu-Chong Wang, Ming-Hui Zhu, Hengjiang Cong, and Wen-Bo Liu. "Pd-catalyzed arylation/aza-Michael addition cascade to C2-spiroindolines and azabicyclo[3.2.2]nonanones." Chemical Communications 56, no. 80 (2020): 12013–16. http://dx.doi.org/10.1039/d0cc04935b.

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22

Takagi, Koji, Hidetoshi Tanaka, and Koichiro Mikami. "Ladderization of polystyrene derivatives by palladium-catalyzed polymer direct arylation." Polymer Chemistry 10, no. 21 (2019): 2647–52. http://dx.doi.org/10.1039/c9py00359b.

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23

Pankow, Robert M., Liwei Ye, and Barry C. Thompson. "Copper catalyzed synthesis of conjugated copolymers using direct arylation polymerization." Polymer Chemistry 9, no. 30 (2018): 4120–24. http://dx.doi.org/10.1039/c8py00913a.

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24

Liu, Can, Zhiming Wang, Lei Wang, Pinhua Li, and Yicheng Zhang. "Palladium-catalyzed direct C2-arylation of azoles with aromatic triazenes." Organic & Biomolecular Chemistry 17, no. 41 (2019): 9209–16. http://dx.doi.org/10.1039/c9ob01883b.

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25

Liu, Yuxia, Dong Xue, Chao Wang, and Linjuan Huang. "Room-Temperature Palladium(II)-Catalyzed Direct 2-Arylation of Indoles with Tetraarylstannanes." Synlett 31, no. 16 (2020): 1613–18. http://dx.doi.org/10.1055/s-0040-1707196.

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A palladium(II)-catalyzed direct 2-arylation of indoles by tetraarylstannanes with oxygen (balloon) as the oxidant at room temperature has been developed. Various tetraarylstannanes can be employed as aryl sources for 2-arylation of indoles in up to 89% yield, providing a practical and efficient catalytic protocol for accessing 2-arylindoles.

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26

Ling, Peng-Xiang, Kai Chen, and Bing-Feng Shi. "Palladium-catalyzed interannular meta-C–H arylation." Chemical Communications 53, no. 13 (2017): 2166–69. http://dx.doi.org/10.1039/c7cc00110j.

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27

Dodonova, Jelena, and Sigitas Tumkevicius. "Access to 6-arylpyrrolo[2,3-d]pyrimidines via a palladium-catalyzed direct C–H arylation reaction." RSC Adv. 4, no. 68 (2014): 35966–74. http://dx.doi.org/10.1039/c4ra07088g.

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28

Gao, Ke, Keita Yamamoto, Keisuke Nogi, and Hideki Yorimitsu. "Palladium-Catalyzed Arylation of Benzylic C–H Bonds of Azaarylmethanes with Aryl Sulfides." Synlett 28, no. 20 (2017): 2956–60. http://dx.doi.org/10.1055/s-0036-1589098.

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Benzylic C–H arylation of azaarylmethanes with aryl sulfides has been developed by using a Pd-NHC catalyst and an amide base. Various azaarylmethanes and aryl sulfides were involved in the reaction to afford the corresponding diarylmethanes in good to excellent yields. Moreover, triarylmethane synthesis was accomplished through iterative arylations of 2- or 4-methylpyridine with two different aryl sulfides.

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29

Gildner, Peter G., Andrew DeAngelis, and Thomas J. Colacot. "Palladium-Catalyzed N-Arylation of Cyclopropylamines." Organic Letters 18, no. 6 (2016): 1442–45. http://dx.doi.org/10.1021/acs.orglett.6b00377.

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30

Rong, Lingling, Qiancai Liu, Yingbo Shi, and Jie Tang. "Fluoradenes via palladium-catalyzed intramolecular arylation." Chemical Communications 47, no. 7 (2011): 2155. http://dx.doi.org/10.1039/c0cc05004k.

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31

Cho, Gae Young, та Carsten Bolm. "Palladium-Catalyzed α-Arylation of Sulfoximines". Organic Letters 7, № 7 (2005): 1351–54. http://dx.doi.org/10.1021/ol050176b.

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32

Hartwig, J., та T. Hama. "Palladium-Catalyzed α-Arylation of Esters". Synfacts 2008, № 7 (2008): 0750. http://dx.doi.org/10.1055/s-2008-1077836.

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33

Okazawa, Toru, Tetsuya Satoh, Masahiro Miura, and Masakatsu Nomura. "Palladium-Catalyzed Multiple Arylation of Thiophenes." Journal of the American Chemical Society 124, no. 19 (2002): 5286–87. http://dx.doi.org/10.1021/ja0259279.

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34

Chuprakov, Stepan, Michael Rubin, and Vladimir Gevorgyan. "Direct Palladium-Catalyzed Arylation of Cyclopropenes." Journal of the American Chemical Society 127, no. 11 (2005): 3714–15. http://dx.doi.org/10.1021/ja042380k.

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35

Palucki, Michael, та Stephen L. Buchwald. "Palladium-Catalyzed α-Arylation of Ketones". Journal of the American Chemical Society 119, № 45 (1997): 11108–9. http://dx.doi.org/10.1021/ja972593s.

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36

Gryko, Daniel T., Olena Vakuliuk, Dorota Gryko, and Beata Koszarna. "Palladium-Catalyzed 2-Arylation of Pyrroles." Journal of Organic Chemistry 74, no. 24 (2009): 9517–20. http://dx.doi.org/10.1021/jo902124c.

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37

Rampon, Daniel S., Ludger A. Wessjohann, and Paulo H. Schneider. "Palladium-Catalyzed Direct Arylation of Selenophene." Journal of Organic Chemistry 79, no. 13 (2014): 5987–92. http://dx.doi.org/10.1021/jo500094t.

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38

Durbin, Matthew J., та Michael C. Willis. "Palladium-Catalyzed α-Arylation of Oxindoles". Organic Letters 10, № 7 (2008): 1413–15. http://dx.doi.org/10.1021/ol800141t.

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39

Song, Juan, Yali Li, Wei Sun, et al. "Efficient palladium-catalyzed C(sp2)–H activation towards the synthesis of fluorenes." New Journal of Chemistry 40, no. 11 (2016): 9030–33. http://dx.doi.org/10.1039/c6nj02033j.

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40

Sun, Meng, Zhe Wang, Jiaxin Wang, Peiyu Guo, Xiangxiang Chen, and Ya-Min Li. "Palladium-catalyzed decarboxylative ortho-arylation of 2-pyridyl sulfoxides with benzoyl peroxides." Organic & Biomolecular Chemistry 14, no. 45 (2016): 10585–88. http://dx.doi.org/10.1039/c6ob02040b.

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41

Panteleev, Jane, Lei Zhang, and Mark Lautens. "Domino Rhodium-Catalyzed Alkyne Arylation/Palladium-Catalyzed N Arylation: A Mechanistic Investigation." Angewandte Chemie 123, no. 39 (2011): 9255–58. http://dx.doi.org/10.1002/ange.201103692.

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42

Panteleev, Jane, Lei Zhang, and Mark Lautens. "Domino Rhodium-Catalyzed Alkyne Arylation/Palladium-Catalyzed N Arylation: A Mechanistic Investigation." Angewandte Chemie International Edition 50, no. 39 (2011): 9089–92. http://dx.doi.org/10.1002/anie.201103692.

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43

Yan, Zhong, Bo Wu, Xiang Gao та Yong-Gui Zhou. "Enantioselective synthesis of quaternary α-aminophosphonates by Pd-catalyzed arylation of cyclic α-ketiminophosphonates with arylboronic acids". Chemical Communications 52, № 72 (2016): 10882–85. http://dx.doi.org/10.1039/c6cc04096a.

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44

Qiao, Huijie, Suyan Sun, Fan Yang, et al. "Palladium-catalyzed direct C–H arylation of ferrocenecarboxamides with aryl halides." RSC Advances 6, no. 64 (2016): 59319–26. http://dx.doi.org/10.1039/c6ra11972g.

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45

Lao, Ye-Xing, Jia-Qiang Wu, Yunyun Chen, Shang-Shi Zhang, Qingjiang Li, and Honggen Wang. "Palladium-catalyzed methylene C(sp3)–H arylation of the adamantyl scaffold." Organic Chemistry Frontiers 2, no. 10 (2015): 1374–78. http://dx.doi.org/10.1039/c5qo00218d.

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46

Jiang, Huanfeng, Wanfei Yang, Huoji Chen, Jianxiao Li, and Wanqing Wu. "Palladium-catalyzed aerobic oxidative allylic C–H arylation of alkenes with polyfluorobenzenes." Chem. Commun. 50, no. 54 (2014): 7202–4. http://dx.doi.org/10.1039/c4cc02023e.

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47

Pilgrim, Ben S., Alice E. Gatland, Carlos H. A. Esteves, et al. "Palladium-catalyzed enolate arylation as a key C–C bond-forming reaction for the synthesis of isoquinolines." Organic & Biomolecular Chemistry 14, no. 3 (2016): 1065–90. http://dx.doi.org/10.1039/c5ob02320c.

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48

Wang, Bing-Xin, Yang-Jie Mao, Hong-Yan Hao, et al. "Pd-catalysed selective C(sp3)–H arylation and acetoxylation of alcohols." Chemical Communications 55, no. 49 (2019): 7049–52. http://dx.doi.org/10.1039/c9cc02911g.

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49

Ishu, Km, Dharmendra Kumar, Naveen Kumar Maurya, Suman Yadav, Dhananjay Chaudhary, and Malleswara Rao Kuram. "Dicarbofunctionalization of unactivated alkenes by palladium-catalyzed domino Heck/intermolecular direct hetero arylation with heteroarenes." Organic & Biomolecular Chemistry 19, no. 10 (2021): 2243–53. http://dx.doi.org/10.1039/d1ob00195g.

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50

Figliola, Carlotta, Sarah M. Greening, Connor Lamont, Brandon R. Groves, and Alison Thompson. "Decarboxylative arylation of substituted pyrroles N-protected with 2-(trimethylsilyl)ethoxymethyl (SEM)." Canadian Journal of Chemistry 96, no. 6 (2018): 534–42. http://dx.doi.org/10.1139/cjc-2017-0402.

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Palladium-catalyzed decarboxylative arylation is reported using pyrroles N-protected with the 2-(trimethylsilyl)ethoxymethyl (SEM) group and featuring 2-, 3-, and 4-substituents about the pyrrolic framework. In contrast to N-protected pyrroles previously used in decarboxylative arylation, the use of SEM allows deprotection under mild conditions.

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