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Journal articles on the topic 'Palladium catalyzed cross-coupling'

Author: Grafiati

Published: 4 June 2021

Last updated: 11 February 2022

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1

Yang, Yang. "Palladium-Catalyzed Cross-Coupling of Nitroarenes." Angewandte Chemie International Edition 56, no. 50 (2017): 15802–4. http://dx.doi.org/10.1002/anie.201708940.

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2

Stradiotto, M., and R. Lundgren. "Palladium-Catalyzed Cross-Coupling with Hydrazine." Synfacts 2011, no. 02 (2011): 0204. http://dx.doi.org/10.1055/s-0030-1259236.

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3

Sain, Shalu, Sonika Jain, Manish Srivastava, Rajendra Vishwakarma, and Jaya Dwivedi. "Application of Palladium-Catalyzed Cross-Coupling Reactions in Organic Synthesis." Current Organic Synthesis 16, no. 8 (2020): 1105–42. http://dx.doi.org/10.2174/1570179416666191104093533.

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: Palladium-catalyzed cross-coupling reactions have gained a continuously growing interest of synthetic organic chemists. The present review gives a brief account of applications of the palladium-catalyzed cross-coupling reactions in comprehensive synthesis, viz., the Heck, Stille, Suzuki–Miyaura, Negishi, Sonogashira, Buchwald–Hartwig, Ullmann and the Oxidative, decarboxylative cross-coupling reactions, with particular emphasis on the synthesis of heterocyclic compounds.

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4

Yuasa, Akihiro, Kazunori Nagao та Hirohisa Ohmiya. "Allylic cross-coupling using aromatic aldehydes as α-alkoxyalkyl anions". Beilstein Journal of Organic Chemistry 16 (7 лютого 2020): 185–89. http://dx.doi.org/10.3762/bjoc.16.21.

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The allylic cross-coupling using aromatic aldehydes as α-alkoxyalkyl anions is described. The synergistic palladium/copper-catalyzed reaction of aromatic aldehydes, allylic carbonates, and a silylboronate produces the corresponding homoallylic alcohol derivatives. This process involves the catalytic formation of a nucleophilic α-silyloxybenzylcopper(I) species and the subsequent palladium-catalyzed allylic substitution.

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5

Zhang, Zhen, Zongyang Li, Bin Fu, and Zhenhua Zhang. "Palladium-catalyzed cross-coupling reaction of azides with isocyanides." Chemical Communications 51, no. 91 (2015): 16312–15. http://dx.doi.org/10.1039/c5cc05981j.

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6

Gagnon, A., M. Duplessis, P. Alsabeh, and F. Barabé. "Palladium-Catalyzed Cross-Coupling Reactions with Tricyclopropylbismuth." Synfacts 2008, no. 7 (2008): 0744. http://dx.doi.org/10.1055/s-2008-1077832.

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7

Orellana, Arturo, David Rosa, Andrei Nikolaev, and Nisha Nithiy. "Palladium-Catalyzed Cross-Coupling Reactions of Cyclopropanols." Synlett 26, no. 04 (2015): 441–48. http://dx.doi.org/10.1055/s-0034-1380156.

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8

Becica, Joseph, Oliver R. J. Heath, Cameron H. M. Zheng, and David C. Leitch. "Palladium‐Catalyzed Cross‐Coupling of Alkenyl Carboxylates." Angewandte Chemie 132, no. 39 (2020): 17430–34. http://dx.doi.org/10.1002/ange.202006586.

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9

Becica, Joseph, Oliver R. J. Heath, Cameron H. M. Zheng, and David C. Leitch. "Palladium‐Catalyzed Cross‐Coupling of Alkenyl Carboxylates." Angewandte Chemie International Edition 59, no. 39 (2020): 17277–81. http://dx.doi.org/10.1002/anie.202006586.

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10

Vaaland, Ingrid Caroline, and Magne Olav Sydnes. "Consecutive Palladium Catalyzed Reactions in One-Pot Reactions." Mini-Reviews in Organic Chemistry 17, no. 5 (2020): 559–69. http://dx.doi.org/10.2174/1570193x16666190716150048.

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Combining palladium catalyzed reactions in one-pot reactions represents an efficient and economical use of catalyst. The Suzuki-Miyaura cross-coupling has been proven to be a reaction which can be combined with other palladium catalyzed reactions in the same pot. This mini-review will highlight some of the latest examples where Suzuki-Miyaura cross-coupling reactions have been combined with other palladium catalyzed reactions in one-pot reaction. Predominantly, examples with homogeneous reaction conditions will be discussed in addition to a few examples from the authors where Pd/C have been us

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11

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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12

Kanwal, Iram, Aqsa Mujahid, Nasir Rasool, et al. "Palladium and Copper Catalyzed Sonogashira cross Coupling an Excellent Methodology for C-C Bond Formation over 17 Years: A Review." Catalysts 10, no. 4 (2020): 443. http://dx.doi.org/10.3390/catal10040443.

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Sonogashira coupling involves coupling of vinyl/aryl halides with terminal acetylenes catalyzed by transition metals, especially palladium and copper. This is a well known reaction in organic synthesis and plays a role in sp2-sp C-C bond formations. This cross coupling was used in synthesis of natural products, biologically active molecules, heterocycles, dendrimers, conjugated polymers and organic complexes. This review paper focuses on developments in the palladium and copper catalyzed Sonogashira cross coupling achieved in recent years concerning substrates, different catalyst systems and r

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13

Akkarasamiyo, Sunisa, Somsak Ruchirawat, Poonsaksi Ploypradith та Joseph S. M. Samec. "Transition-Metal-Catalyzed Suzuki–Miyaura-Type Cross-Coupling Reactions of π-Activated Alcohols". Synthesis 52, № 05 (2020): 645–59. http://dx.doi.org/10.1055/s-0039-1690740.

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The Suzuki–Miyaura reaction is one of the most powerful tools for the formation of carbon–carbon bonds in organic synthesis. The utilization of alcohols in this powerful reaction is a challenging task. This short review covers progress in the transition-metal-catalyzed Suzuki–Miyaura-type cross-coupling reaction of π-activated alcohol, such as aryl, benzylic, allylic, propargylic and allenic alcohols, between 2000 and June 2019.1 Introduction2 Suzuki–Miyaura Cross-Coupling Reactions of Aryl Alcohols2.1 One-Pot Reactions with Pre-activation of the C–O Bond2.1.1 Palladium Catalysis2.1.2 Nickel

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14

Shi, Yili, Stephen D. Ramgren, and Suzanne A. Blum. "Palladium-Catalyzed Carboauration of Alkynes and Palladium/Gold Cross-Coupling." Organometallics 28, no. 5 (2009): 1275–77. http://dx.doi.org/10.1021/om801206g.

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15

Zhou, Tongliang, and Michal Szostak. "Palladium-catalyzed cross-couplings by C–O bond activation." Catalysis Science & Technology 10, no. 17 (2020): 5702–39. http://dx.doi.org/10.1039/d0cy01159b.

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16

Daley, Ryan A., and Joseph J. Topczewski. "Aryl-Decarboxylation Reactions Catalyzed by Palladium: Scope and Mechanism." Synthesis 52, no. 03 (2019): 365–77. http://dx.doi.org/10.1055/s-0039-1690769.

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Palladium-catalyzed cross-couplings and related reactions have enabled many transformations essential to the synthesis of pharmaceuticals, agrochemicals, and organic materials. A related family of reactions that have received less attention are decarboxylative functionalization reactions. These reactions replace the preformed organometallic precursor (e.g., boronic acid or organostannane) with inexpensive and readily available carboxylic acids for many palladium-catalyzed reactions. This review focuses on catalyzed reactions where the elementary decarboxylation step is thought to occur at a pa

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17

MIYAURA, Norio. "Palladium-Catalyzed Cross-Coupling Reactions in Organic Syntheses." TRENDS IN THE SCIENCES 16, no. 5 (2011): 13–17. http://dx.doi.org/10.5363/tits.16.5_13.

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18

Miyaura, Norio, and Akira Suzuki. "Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds." Chemical Reviews 95, no. 7 (1995): 2457–83. http://dx.doi.org/10.1021/cr00039a007.

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19

Kang, Suk-Ku, Hong-Woo Lee, Jae-Sun Kim, and Sang-Chul Choi. "Palladium-catalyzed cross-coupling of organostannanes with iodanes." Tetrahedron Letters 37, no. 21 (1996): 3723–26. http://dx.doi.org/10.1016/0040-4039(96)00669-7.

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20

So, Chau Ming, and Fuk Yee Kwong. "Palladium-catalyzed cross-coupling reactions of aryl mesylates." Chemical Society Reviews 40, no. 10 (2011): 4963. http://dx.doi.org/10.1039/c1cs15114b.

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21

Al-hassan, Mohammed I. "Synthesis of Clomid Using Palladium-Catalyzed Cross-Coupling." Synthetic Communications 17, no. 15 (1987): 1787–96. http://dx.doi.org/10.1080/00397918708077323.

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22

Zhao, Yiming, Huy van Nguyen, Louise Male, Philip Craven, Benjamin R. Buckley, and John S. Fossey. "Phosphino-Triazole Ligands for Palladium-Catalyzed Cross-Coupling." Organometallics 37, no. 22 (2018): 4224–41. http://dx.doi.org/10.1021/acs.organomet.8b00539.

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23

Hillerich, Jens, and Herbert Plenio. "Continuous biphasic catalysis: palladium catalyzed cross coupling reactions." Chemical Communications, no. 24 (2003): 3024. http://dx.doi.org/10.1039/b310504k.

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24

Kang, Dongjin, Dahan Eom, Hyunseok Kim, and Phil Ho Lee. "Palladium-Catalyzed Multialkynyl Cross-Coupling Reactions with Tetraalkynylindates." European Journal of Organic Chemistry 2010, no. 12 (2010): 2330–36. http://dx.doi.org/10.1002/ejoc.201000027.

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25

Nicolaou, K. C., Paul G. Bulger, and David Sarlah. "Palladium-Catalyzed Cross-Coupling Reactions in Total Synthesis." Angewandte Chemie International Edition 44, no. 29 (2005): 4442–89. http://dx.doi.org/10.1002/anie.200500368.

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26

Endo, Mayuko, Keigo Fugami, Tatsuki Enokido, Hiroshi Sano, and Masanori Kosugi. "Palladium-Catalyzed Cross-Coupling Reaction Using Arylgermanium Sesquioxide." Advanced Synthesis & Catalysis 349, no. 7 (2007): 1025–27. http://dx.doi.org/10.1002/adsc.200700002.

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27

Monguchi, Yasunari, Tomohiro Hattori, Yasuhiro Miyamoto, Takayoshi Yanase, Yoshinari Sawama, and Hironao Sajiki. "Palladium on Carbon-Catalyzed Cross-Coupling using Triarylbismuths." Advanced Synthesis & Catalysis 354, no. 13 (2012): 2561–67. http://dx.doi.org/10.1002/adsc.201200179.

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28

Denmark, Scott E., and Daniel Wehrli. "Highly Stereospecific, Palladium-Catalyzed Cross-Coupling of Alkenylsilanols." Organic Letters 2, no. 4 (2000): 565–68. http://dx.doi.org/10.1021/ol005565e.

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29

Bew, Sean, and J. Sweeney. "Palladium-Catalyzed Cross-Coupling Reactions of 3-Tributylstannylsulfolene." Synlett 1997, no. 11 (1997): 1273–74. http://dx.doi.org/10.1055/s-1997-1020.

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30

Al-Hassan, Mohammed I. "Synthesis of broparestrol using palladium-catalyzed cross-coupling." Journal of Organometallic Chemistry 321, no. 1 (1987): 119–21. http://dx.doi.org/10.1016/0022-328x(87)80330-3.

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31

Pan, Changduo, Miaochang Liu, Lin Zhang, Huayue Wu, Jinchang Ding, and Jiang Cheng. "Palladium catalyzed ligand-free Suzuki cross-coupling reaction." Catalysis Communications 9, no. 4 (2008): 508–10. http://dx.doi.org/10.1016/j.catcom.2007.06.022.

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32

Chen, Zicong, and Chau Ming So. "Palladium‐Phenylpyrazolylphosphine‐Catalyzed Cross‐Coupling of Alkenyl Pivalates." Asian Journal of Organic Chemistry 10, no. 4 (2021): 776–79. http://dx.doi.org/10.1002/ajoc.202100031.

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33

Wang, Jianbo, and Kang Wang. "Transition-Metal-Catalyzed Cross-Coupling with Non-Diazo Carbene Precursors." Synlett 30, no. 05 (2018): 542–51. http://dx.doi.org/10.1055/s-0037-1611020.

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Transition-metal-catalyzed cross-coupling reactions through metal carbene migratory insertion have emerged as powerful methodology for carbon–carbon bond constructions. Typically, diazo compounds (or in situ generated diazo compounds from N-tosylhydrazones) have been employed as the metal carbene precursors for this type of cross-coupling reactions. Recently, cross-coupling reactions employing non-diazo carbene precursors, such as conjugated ene-yne-ketones, allenyl ketones, alkynes, cyclopropenes, and Cr(0) Fischer carbenes, have been developed. This account will summarize our efforts in the

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34

Zhang, Hang, Bo Wang, Kang Wang, et al. "Pd-Catalyzed ring-opening cross-coupling of cyclopropenes with aryl iodides." Chem. Commun. 50, no. 59 (2014): 8050–52. http://dx.doi.org/10.1039/c4cc03651d.

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35

Luo, Haiqing, Guojiao Wu, Shuai Xu, et al. "Palladium-catalyzed cross-coupling of aryl fluorides with N-tosylhydrazones via C–F bond activation." Chemical Communications 51, no. 68 (2015): 13321–23. http://dx.doi.org/10.1039/c5cc05035a.

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A palladium-catalyzed cross-coupling reaction of electron-deficient aryl fluorides with aryl N-tosylhydrazones, which involves C–F bond activation and migratory insertion of palladium carbene, has been developed.

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36

Ma, Hongpeng, Chaolumen Bai, and Yong-Sheng Bao. "Heterogeneous Suzuki–Miyaura coupling of heteroaryl ester via chemoselective C(acyl)–O bond activation." RSC Advances 9, no. 30 (2019): 17266–72. http://dx.doi.org/10.1039/c9ra02394a.

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37

Shimizu, Masaki, Ikuhiro Nagao, Shin-ichi Kiyomoto, and Tamejiro Hiyama. "New Synthesis of Dibenzofulvenes by Palladium-Catalyzed Double Cross-Coupling Reactions." Australian Journal of Chemistry 65, no. 9 (2012): 1277. http://dx.doi.org/10.1071/ch12060.

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Palladium-catalyzed double cross-coupling reactions of 1,1-bis(pinacolato)borylalk-1-enes with 2,2′-dibromobiaryls and of 9-stannafluorenes with 1,1-dibromoalk-1-enes have been demonstrated to serve as new synthetic methods for dibenzofulvenes.

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38

Miao, Hui, Fenhua Wang, Shuangliu Zhou, Guangchao Zhang, and Yang Li. "Palladium-catalyzed Hiyama coupling reaction of arylsulfonyl hydrazides under oxygen." Organic & Biomolecular Chemistry 13, no. 16 (2015): 4647–51. http://dx.doi.org/10.1039/c5ob00139k.

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Palladium-catalyzed Hiyama cross-coupling reactions of various arylsulfonyl hydrazides with a wide variety of aryl silanes have been achieved in good to excellent yields under simple aerobic conditions.

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39

Schmidt, Bernd, Nastja Riemer, Christin Coswig, and Mike Shipman. "Palladium-Catalyzed Cross-Coupling of Arenediazonium Salts with Organoindium or Organobismuth Reagents." Synlett 29, no. 18 (2018): 2427–31. http://dx.doi.org/10.1055/s-0037-1611001.

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40

Kramer, Søren. "Homogeneous Gold-Catalyzed Aryl–Aryl Coupling Reactions." Synthesis 52, no. 14 (2020): 2017–30. http://dx.doi.org/10.1055/s-0039-1690882.

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Synthesis of biaryl motifs are crucial for the development and synthesis of pharmaceuticals, natural products, and functional materials. During the last decade, gold-catalyzed aryl–aryl coupling reactions have evolved from a curiosity to a well-established research field. This review summarizes the field from early examples up to the latest developments. Facile C–H functionalization and orthogonal reactivity compared to many other types of transition metal catalysis, for example, palladium catalysis, makes gold-catalyzed aryl–aryl coupling reactions highly appealing and valuable.1 Introduction

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41

Len, Christophe. "Catalysts for Suzuki–Miyaura Coupling Reaction." Catalysts 10, no. 1 (2020): 50. http://dx.doi.org/10.3390/catal10010050.

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42

Guo, Meng, Zhen Wei, Jianming Yang, Zunyuan Xie та Weiqiang Zhang. "α, β-Alkynone Accelerated PPM Level Pd-Catalyzed Sonogashira Coupling Reaction". Catalysts 10, № 3 (2020): 302. http://dx.doi.org/10.3390/catal10030302.

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In the palladium-catalyzed C−C coupling reaction, electron-rich phosphine ligands and a catalytic amount of catalyst loading are required in most cases. Herein, a bench-stable, easily modified and less toxic alkynone was utilized in palladium-catalyzed Sonogashira coupling to replace conventional phosphine ligands. With 1-(4-methoxyphenyl)-3-phenyl-2-yn-1-one (L2) as the ligand, catalyst loading was reduced to 5-10 ppm. In this newly developed catalytic system, a variety of (hetero)arene iodines and alkynes could be tolerated, resulting in good yields of the corresponding cross-coupling produc

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43

Ma, Cong, Chuan-Qi Zhao, Yi-Qian Li, et al. "Palladium-catalyzed C–H activation/C–C cross-coupling reactions via electrochemistry." Chemical Communications 53, no. 90 (2017): 12189–92. http://dx.doi.org/10.1039/c7cc07429h.

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44

Stein, A. L., F. N. Bilheri, and G. Zeni. "Application of organoselenides in the Suzuki, Negishi, Sonogashira and Kumada cross-coupling reactions." Chemical Communications 51, no. 85 (2015): 15522–25. http://dx.doi.org/10.1039/c5cc06347g.

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45

Feng, Boya, Yudong Yang, and Jingsong You. "Palladium-catalyzed denitrative Sonogashira-type cross-coupling of nitrobenzenes with terminal alkynes." Chemical Communications 56, no. 5 (2020): 790–93. http://dx.doi.org/10.1039/c9cc08663c.

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46

Guo, Tao, Jing-Jing Liang, Song Yang, et al. "Palladium-catalyzed oxidative C–H/C–H cross-coupling of imidazopyridines with azoles." Organic & Biomolecular Chemistry 16, no. 33 (2018): 6039–46. http://dx.doi.org/10.1039/c8ob01263f.

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47

Markovic, Tim, Benjamin N. Rocke, David C. Blakemore, Vincent Mascitti, and Michael C. Willis. "Pyridine sulfinates as general nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions with aryl halides." Chemical Science 8, no. 6 (2017): 4437–42. http://dx.doi.org/10.1039/c7sc00675f.

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Pyridine sulfinates are stable and straightforward to prepare nucleophilic coupling partners for palladium catalyzed cross-coupling reactions with aryl and heteroaryl halides. The scope with respect to the halides coupling partner is considerable, and allows the preparation of a broad range of linked pyridines.

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48

Liu, Xia, Ze Yi, Jianhui Wang, and Guiyan Liu. "Decarboxylative acylation of arenes with mandelic acid derivatives via palladium-catalyzed oxidative sp2 C–H activation." RSC Advances 5, no. 14 (2015): 10641–46. http://dx.doi.org/10.1039/c4ra14107e.

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49

Friesen, Richard W., Richard W. Loo, and Claudio F. Sturino. "The preparation of C-aryl glucals via palladium-catalyzed cross-coupling methods." Canadian Journal of Chemistry 72, no. 5 (1994): 1262–72. http://dx.doi.org/10.1139/v94-160.

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The C-aryl glucals 17–31 have been prepared by the palladium-catalyzed cross coupling of 1-tributylstannyl-3,4,6-tri-O-(tert-butyldimethylsilyl)-D-glucal (11) and aryl bromides. The major by-product in all of these reactions is the dimer 33, the product of homocoupling of 11. Alternatively, the C-aryl glucals 34–40 can be obtained from the palladium-catalyzed coupling of 1-iodo-3,4,6-tri-O-(triisopropylsilyl)-D-glucal (16) and a variety of metalated aromatics, including ArZnCl, ArB(OH)2, and ArB(OMe)2. The advantages of the latter procedure include superior coupling yields under milder reactio

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50

Wang, Tao, Shuwu Yang, Silin Xu, Chunyu Han, Ge Guo, and Junfeng Zhao. "Palladium catalyzed Suzuki cross-coupling of benzyltrimethylammonium salts via C–N bond cleavage." RSC Advances 7, no. 26 (2017): 15805–8. http://dx.doi.org/10.1039/c7ra02549a.

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A Pd catalyzed Suzuki cross-coupling of a benzyltrimethylammonium salt is described. This reaction offers a highly efficient approach to diarylmethanes and also paves the way for the application of benzyltrimethylammonium salts in Pd catalyzed cross-coupling reactions.

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