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Journal articles on the topic 'Palladium-catalyzed cross couplings in organic synthesis'

Author: Grafiati

Published: 3 June 2025

Last updated: 31 July 2025

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1

Collet, Jurriën W., Thomas R. Roose, Bram Weijers, Bert U. W. Maes, Eelco Ruijter, and Romano V. A. Orru. "Recent Advances in Palladium-Catalyzed Isocyanide Insertions." Molecules 25, no. 21 (2020): 4906. http://dx.doi.org/10.3390/molecules25214906.

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Isocyanides have long been known as versatile chemical reagents in organic synthesis. Their ambivalent nature also allows them to function as a CO-substitute in palladium-catalyzed cross couplings. Over the past decades, isocyanides have emerged as practical and versatile C1 building blocks, whose inherent N-substitution allows for the rapid incorporation of nitrogeneous fragments in a wide variety of products. Recent developments in palladium catalyzed isocyanide insertion reactions have significantly expanded the scope and applicability of these imidoylative cross-couplings. This review high

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2

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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3

Rifhat Bibi, Rifhat Bibi, Muhammad Yaseen Muhammad Yaseen, Haseen Ahmad Haseen Ahmad, Ismat Ullah Khan Ismat Ullah Khan, Shaista Parveen Shaista Parveen, and Abbas Hassan Abbas Hassan. "Palladium Catalyzed Synthesis of Phenylquinoxaline-Alkyne Derivatives via Sonogashira Cross Coupling Reaction." Journal of the chemical society of pakistan 43, no. 1 (2021): 95. http://dx.doi.org/10.52568/000550.

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Transition metals mediated cross coupling methodologies provide an extremely powerful versatile pathway in organic syntheses undoubtedly, a facile route for syntheses and derivatization of biologically important heterocycles from easily available precursors. Sonogashira coupling reaction, a leading method to Csp-Csp2 bond formation is one of the most important and rapid pathways to couple aryl/vinyl halides with terminal alkynes. Current research study deals with the synthesis of alkyne substituted quinoxaline derivatives. The quinoxalines class of aromatic heterocycles exhibits a wide variety

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4

Rifhat Bibi, Rifhat Bibi, Muhammad Yaseen Muhammad Yaseen, Haseen Ahmad Haseen Ahmad, Ismat Ullah Khan Ismat Ullah Khan, Shaista Parveen Shaista Parveen, and Abbas Hassan Abbas Hassan. "Palladium Catalyzed Synthesis of Phenylquinoxaline-Alkyne Derivatives via Sonogashira Cross Coupling Reaction." Journal of the chemical society of pakistan 43, no. 1 (2021): 95. http://dx.doi.org/10.52568/000550/jcsp/43.01.2021.

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Transition metals mediated cross coupling methodologies provide an extremely powerful versatile pathway in organic syntheses undoubtedly, a facile route for syntheses and derivatization of biologically important heterocycles from easily available precursors. Sonogashira coupling reaction, a leading method to Csp-Csp2 bond formation is one of the most important and rapid pathways to couple aryl/vinyl halides with terminal alkynes. Current research study deals with the synthesis of alkyne substituted quinoxaline derivatives. The quinoxalines class of aromatic heterocycles exhibits a wide variety

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5

Rifhat Bibi, Rifhat Bibi, Muhammad Yaseen Muhammad Yaseen, Haseen Ahmad Haseen Ahmad, Ismat Ullah Khan Ismat Ullah Khan, Shaista Parveen Shaista Parveen, and Abbas Hassan Abbas Hassan. "Palladium Catalyzed Synthesis of Phenylquinoxaline-Alkyne Derivatives via Sonogashira Cross Coupling Reaction." Journal of the chemical society of pakistan 43, no. 1 (2021): 95. http://dx.doi.org/10.52568/000009.

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Transition metals mediated cross coupling methodologies provide an extremely powerful versatile pathway in organic syntheses undoubtedly, a facile route for syntheses and derivatization of biologically important heterocycles from easily available precursors. Sonogashira coupling reaction, a leading method to Csp-Csp2 bond formation is one of the most important and rapid pathways to couple aryl/vinyl halides with terminal alkynes. Current research study deals with the synthesis of alkyne substituted quinoxaline derivatives. The quinoxalines class of aromatic heterocycles exhibits a wide variety

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6

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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7

Li, Jie, and Paul Knochel. "Chromium-Catalyzed Cross-Couplings and Related Reactions." Synthesis 51, no. 10 (2019): 2100–2106. http://dx.doi.org/10.1055/s-0037-1611756.

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Transition-metal-catalyzed cross-couplings have been recognized as a powerful tool for sustainable syntheses. Despite the fact that remarkable progress was achieved by palladium and nickel catalysis, the high price and toxicity still remained a drawback. Recently, naturally more abundant and less toxic low-valent chromium salts, such as Cr(II) and Cr(III) chlorides, displayed notable unique catalytic reactivity. Thus, recent progress in the field of chromium-catalyzed cross-couplings and related reactions are highlighted in the present short review until December 2018.1 Introduction and Early

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8

Ji, Yuan, Ning Zhong, Zinan Kang, Guobing Yan, and Ming Zhao. "Synthesis of Internal Alkynes through an Effective Tandem Elimination–Hydrodebromination–Cross-Coupling of gem-Dibromoalkenes with Halobenzenes." Synlett 29, no. 02 (2017): 209–14. http://dx.doi.org/10.1055/s-0036-1590907.

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Carbon–carbon couplings are among the most important strategies for constructing functional molecules in organic synthetic chemistry, and cheap, diverse, and readily available coupling partners are crucial to these diverse reactions. In this contribution, we report the first palladium-catalyzed C–C cross-coupling reaction of two kinds of organic halide, a gem-dibromoalkene and a halobenzene, as the starting materials. Terminal alkynes were generated in situ through a tandem elimination–hydrodebromination process, and the internal alkyne final products were synthesized in one pot. The reaction

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9

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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10

Zaman, Abdalhussein Ibadi Alaridhee, Hasan Nada, Dohan Abid Muhand, Jabbar Radhi Ali, and Wheed Radhi Ahmed. "Study of mechanistic pathways in cross-linking reactions with palladium." Journal of Wildlife and Biodiversity 7, Special Issue (2023): 664–75. https://doi.org/10.5281/zenodo.10307342.

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Palladium-catalyzed cross-coupling reactions, including the Suzuki, Stille, and Negishi couplings, have emerged as essential methodologies in contemporary organic synthesis. Nevertheless, there is still a lack of comprehensive understanding of the molecular processes involved in these significant events that lead to the formation of C-C and C-heteroatom bonds. This paper provides a complete analysis of the fundamental mechanistic investigations conducted on the primary cross-coupling processes facilitated by palladium catalysts. The present study focuses on the examination of kinetic aspects o

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11

Mukai, Shoma, and Nathan Werner. "Synthesis and Palladium-Catalyzed Cross-Coupling of an Alkyl-Substituted Alkenylboronic Acid Pinacol Ester with Aryl Bromides." American Journal of Undergraduate Research 20, no. 1 (2023): 37–46. http://dx.doi.org/10.33697/ajur.2023.078.

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The palladium-catalyzed cross-coupling reaction of alkyl-substituted alkenylboron reagents with aryl halides is a versatile method to introduce a hydrophobic hydrocarbon chain onto organic compounds of interest. The application of the cross-coupling reaction is enabled by synthetic methods for the preparation of alkenylboron reagents. The geometrically pure, alkyl-substituted alkenylboron reagent, (E)-octenylboronic acid pinacol ester, was prepared by 9-BBN-catalyzed hydroboration reaction of 1-octene with pinacolborane in refluxing 1 M THF solution. This reagent was then evaluated in palladiu

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12

Dong, Zhi-Bing, and Jin-Quan Chen. "Recent Progress in Utilization of Functionalized Organometallic Reagents in Cross Coupling Reactions and Nucleophilic Additions." Synthesis 52, no. 24 (2020): 3714–34. http://dx.doi.org/10.1055/s-0040-1706550.

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AbstractOrganometallic compounds have become increasingly important in organic synthesis because of their high chemoselectivity and excellent reactivity. Recently, a variety of organometallic reagents were found to facilitate transition-metal-catalyzed cross-coupling reactions and nucleophilic addition reactions. Here, we have summarized the latest progress in cross-coupling reactions and in nucleophilic addition reactions with functionalized organometallic reagents present to illustrate their application value. Due to the tremendous contribution made by the Knochel group towards the developme

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13

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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14

Serban, Georgeta, та Faïza Diaba. "Palladium-Catalyzed α-Arylation of Esters: Synthesis of the Tetrahydroisoquinoline Ring". Reactions 6, № 1 (2025): 17. https://doi.org/10.3390/reactions6010017.

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The palladium-catalyzed cross-coupling reaction used for carbon–carbon bond formation is one of the most commonly applied reactions in modern organic synthesis. In this work, a concise strategy was developed for constructing the tetrahydroisoquinoline core, a key structural motif found in many biologically active compounds. This method involves the palladium-catalyzed intramolecular coupling of aryl iodides with ester enolates generated in the presence of K3PO4 as a base, resulting in the formation of the tetrahydroisoquinoline ring with an exceptionally high yield of 84%.

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15

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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16

He, Ping, Cheng-Guo Dong, and Qiao-Sheng Hu. "Synthesis of hindered biphenyls by sequential non-transition metal-catalyzed reaction/palladium-catalyzed cross-couplings." Tetrahedron Letters 49, no. 12 (2008): 1906–9. http://dx.doi.org/10.1016/j.tetlet.2008.01.101.

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17

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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18

Mao, Zhenjun, Haorui Gu, and Xufeng Lin. "Recent Advances of Pd/C-Catalyzed Reactions." Catalysts 11, no. 9 (2021): 1078. http://dx.doi.org/10.3390/catal11091078.

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The Pd/C-catalyzed reactions, including reduction reactions and cross-coupling reactions, play an irreplaceable role in modern organic synthesis. Compared to the homogeneous palladium catalyst system, the heterogeneous Pd/C catalyst system offers an alternative protocol that has particular advantages and applications. Herein, a review on Pd/C-catalyzed reactions is presented. Both the advances in Pd/C-catalyzed methodologies and the application of Pd/C-catalysis in total synthesis are covered in this review.

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19

Vyvyan, James R., Celeste Loitz, Ryan E. Looper, Cheryl S. Mattingly, Emily A. Peterson, and Steven T. Staben. "Synthesis of Aromatic Bisabolene Natural Products via Palladium-Catalyzed Cross-Couplings of Organozinc Reagents†." Journal of Organic Chemistry 69, no. 7 (2004): 2461–68. http://dx.doi.org/10.1021/jo035778s.

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20

Liu, Zhenwei, Nannan Luan, Linhua Shen, et al. "Palladium-Catalyzed Hiyama Cross-Couplings of Arylsilanes with 3-Iodoazetidine: Synthesis of 3-Arylazetidines." Journal of Organic Chemistry 84, no. 19 (2019): 12358–65. http://dx.doi.org/10.1021/acs.joc.9b01715.

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21

Shinde, Vikki N., Shiv Dhiman, Rangan Krishnan, Dalip Kumar, and Anil Kumar. "Synthesis of imidazopyridine-fused indoles via one-pot sequential Knoevenagel condensation and cross dehydrogenative coupling." Organic & Biomolecular Chemistry 16, no. 33 (2018): 6123–32. http://dx.doi.org/10.1039/c8ob01449c.

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22

Zhang, Yanghui, and Bin Wan. "Synthesis of Unsymmetrically Substituted Tetraphenylenes through Palladium-Catalyzed C(sp2)–H Activation." Synthesis 53, no. 18 (2021): 3299–306. http://dx.doi.org/10.1055/a-1416-9737.

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AbstractAn efficient protocol for the palladium-catalyzed cross-coupling reaction of 2-iodobiphenyls with biphenylene has been developed through C–H activation. The reaction provides a simple and efficient method for the synthesis of unsymmetrically substituted tetraphenylenes.

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23

Zhou, Qi, Yunpeng Gao, Yiyang Xiao, et al. "Palladium-catalyzed carbene coupling of N-tosylhydrazones and arylbromides to synthesize cross-conjugated polymers." Polymer Chemistry 10, no. 5 (2019): 569–73. http://dx.doi.org/10.1039/c8py01529e.

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Palladium-catalyzed cross-coupling reactions of N-tosylhydrazones and arylbromides have been applied for the first time in the synthesis of cross-conjugated polymers, namely poly(arylene-1,1-vinylidene)s (iso-PAVs).

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24

Shaaban, Mohamed R., Thoraya A. Farghaly, Afaf Y. Khormi, and Ahmad M. Farag. "Recent Advances in Synthesis and Uses of Heterocycles-based Palladium(II) Complexes as Robust, Stable, and Low-cost Catalysts for Suzuki- Miyaura Crosscouplings." Current Organic Chemistry 23, no. 15 (2019): 1601–62. http://dx.doi.org/10.2174/1385272823666190620121845.

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C-C cross-couplings constitute the largest diversity of organic reactions of chemical, biomedical, and industrial significance. They are also among the most frequently encountered reactions used in the synthesis of numerous drugs and relevant pharmaceutical substances. Development of an easily accessed, efficient, stable, and low cost catalyst is an attractive area of research in such kind of organic synthesis. This review highlights the remarkable and recent achievements made recently in the synthesis and use of palladium(II) complexes catalysts, that are based on heterocycles as ligands in t

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25

El-Maiss, Janwa, Tharwat Mohy El Dine, Chung-Shin Lu, et al. "Recent Advances in Metal-Catalyzed Alkyl–Boron (C(sp3)–C(sp2)) Suzuki-Miyaura Cross-Couplings." Catalysts 10, no. 3 (2020): 296. http://dx.doi.org/10.3390/catal10030296.

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Boron chemistry has evolved to become one of the most diverse and applied fields in organic synthesis and catalysis. Various valuable reactions such as hydroborylations and Suzuki–Miyaura cross-couplings (SMCs) are now considered as indispensable methods in the synthetic toolbox of researchers in academia and industry. The development of novel sterically- and electronically-demanding C(sp3)–Boron reagents and their subsequent metal-catalyzed cross-couplings attracts strong attention and serves in turn to expedite the wheel of innovative applications of otherwise challenging organic adducts in

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26

Yuan, Jinwei, Shuainan Liu, Yongmei Xiao, Pu Mao, Liangru Yang, and Lingbo Qu. "Palladium-catalyzed oxidative amidation of quinoxalin-2(1H)-ones with acetonitrile: a highly efficient strategy toward 3-amidated quinoxalin-2(1H)-ones." Organic & Biomolecular Chemistry 17, no. 4 (2019): 876–84. http://dx.doi.org/10.1039/c8ob03061h.

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27

Kanagasundaram, Thines, Antje Timmermann, Carsten S. Kramer, and Klaus Kopka. "A new approach to silicon rhodamines by Suzuki–Miyaura coupling – scope and limitations." Beilstein Journal of Organic Chemistry 15 (October 29, 2019): 2569–76. http://dx.doi.org/10.3762/bjoc.15.250.

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Background: Silicon rhodamines are of particular interest because of their advantageous dye properties (fluorescence- and biostability, quantum efficiency, tolerance to photobleaching). Therefore, silicon rhodamines find frequent application in STED (stimulated emission depletion) microscopy, as sensor molecules for, e.g., ions and as fluorophores for the optical imaging of tumors. Different strategies were already employed for their synthesis. Because of just three known literature examples in which Suzuki–Miyaura cross couplings gave access to silicon rhodamines in poor to moderate yields, w

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28

Barboza, Amanda Aline, Juliana Arantes Dantas, Guilherme Augusto de Melo Jardim, Marco Antonio Barbosa Ferreira, Mateus Oliveira Costa, and Attilio Chiavegatti. "Recent Advances in Palladium-Catalyzed Oxidative Couplings in the Synthesis/Functionalization of Cyclic Scaffolds Using Molecular Oxygen as the Sole Oxidant." Synthesis 54, no. 09 (2021): 2081–102. http://dx.doi.org/10.1055/a-1701-7397.

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AbstractOver the past years, Pd(II)-catalyzed oxidative couplings have enabled the construction of molecular scaffolds with high structural diversity via C–C, C–N and C–O bond-forming reactions. In contrast to the use of stoichiometric amounts of more common oxidants, such as metal salts (Cu and Ag) and benzoquinone derivatives, the use of molecular oxygen for the direct or indirect regeneration of Pd(II) species presents itself as a more viable alternative in terms of economy and sustainability. In this review, we describe recent advances on the development of Pd-catalyzed oxidative cyclizati

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29

Hassine, Manel, Hichem Ben Jannet, NourEddine Ghermani, Mouad Alami, and Samir Messaoudi. "Synthesis of N-(Hetero)arylconvolvine Derivatives through a Palladium-Catalyzed Buchwald–Hartwig Cross-Coupling." Synthesis 52, no. 03 (2019): 450–58. http://dx.doi.org/10.1055/s-0039-1690238.

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The present study describes the isolation of convolvine from the roots of the Tunisian plant Convolvulus dorycnium L. and its synthesis through a four-step sequence starting from tropine. Then, an efficient synthesis of N-(het)aryltropanes derivatives by a sequence of a palladium-catalyzed N-arylationof convolvine has been established. This strategy enabled access to unknown tropane scaffolds of biological interests.

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30

Lubin-Germain, Nadège, Jacques Augé, Valérie Boucard, Karen Larrieu, and Jacques Uziel. "C -Glycosylated Phenylalanine Synthesis by Palladium-Catalyzed Cross-Coupling Reactions." Synlett, no. 12 (2003): 1834–37. http://dx.doi.org/10.1055/s-2003-41416.

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31

Fu, Jian-min, Yong Chen, and Arlindo L. Castelhano. "Synthesis of Functionalized Pyridones via Palladium Catalyzed Cross Coupling Reactions." Synlett 1998, no. 12 (1998): 1408–10. http://dx.doi.org/10.1055/s-1998-1974.

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32

Zeni, Gilson, Cristina W. Nogueira, Jesus M. Pena, et al. "Stereospecific Synthesis of Chalcogenoenynes by Palladium-Catalyzed Cross-Coupling Reaction." Synlett, no. 4 (2003): 0579–81. http://dx.doi.org/10.1055/s-2003-37519.

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33

Timári, Géza. "Synthesis of Polyfused Heteroaromatics by PalladiumCatalyzed CrossCoupling Reaction." Molecules 1, no. 10 (1997): 236–41. http://dx.doi.org/10.1007/s007830050042.

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34

So, Chau, On Yuen, Wai Pang, Xiangmeng Chen, Zicong Chen, and Fuk Kwong. "Synthesis of Flavone Derivatives through Versatile Palladium-Catalyzed Cross-Coupling Reactions of Tosyloxy- and Mesyloxyflavones." Synlett 30, no. 06 (2019): 731–37. http://dx.doi.org/10.1055/s-0037-1611742.

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Tosyloxy- and mesyloxyflavones derived from abundant and biologically important hydroxyflavones were used to synthesize a series of functionalized flavones through versatile palladium-catalyzed cross-coupling reactions. A Pd(OAc)2/2-[2-(dicyclohexylphosphino)phenyl]-1-methyl-1H-indole system effectively catalyzed the reactions of a broad range of tosyloxy- and mesyloxyflavones as electrophilic coupling partners with various nucleophiles to give the corresponding products in good to excellent yields. Catalyst loadings of as little as 0.1 mol% Pd were successfully used. Importantly, we demonstra

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35

Shu, Xing-Zhong, Xiaobo Pang, and Xuejing Peng. "Reductive Cross-Coupling of Vinyl Electrophiles." Synthesis 52, no. 24 (2020): 3751–63. http://dx.doi.org/10.1055/s-0040-1707342.

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The synthesis of alkenes (olefins) is a central subject in the synthetic community. The transition-metal-catalyzed reductive cross-coupling of vinyl electrophiles has emerged as a promising tool to produce alkenes with improved flexibility, structural complexity, and functionality tolerance. In this review, we summarized the progress in this field with respect to cross-electrophile couplings and reductive Heck reactions using vinyl electrophiles.1 Introduction2 Cross-Electrophile Coupling of Vinyl Electrophiles3 Reductive Heck Reaction of Vinyl Electrophiles4 Summary and Outlook

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Thiyagarajan, Subramanian, та Chidambaram Gunanathan. "Ruthenium-Catalyzed Direct Cross-Coupling of Secondary Alcohols to β-Disubstituted Ketones". Synlett 30, № 18 (2019): 2027–34. http://dx.doi.org/10.1055/s-0037-1611912.

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The β-disubstituted ketone functionality is prevalent in biologically active compounds and in pharmaceuticals. A ruthenium-catalyzed direct synthesis of β-disubstituted ketones by cross-coupling of two different secondary alcohols is reported. This new protocol was applied to the synthesis of variety of β-disubstituted ketones from various cyclic, acyclic, symmetrical, and unsymmetrical secondary alcohols. An amine–amide metal–ligand cooperation in a Ru catalyst facilitates the activation and formation of covalent bonds in selective sequences to provide the products. Kinetic and deuterium-labe

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37

Kotipalli, Ramesh, Attunuri Nagireddy, and Maddi Sridhar Reddy. "Palladium-catalyzed cyclizative cross coupling of ynone oximes with 2-haloaryl N-acrylamides for isoxazolyl indoline bis-heterocycles." Organic & Biomolecular Chemistry 20, no. 13 (2022): 2609–14. http://dx.doi.org/10.1039/d2ob00065b.

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We demonstrated a dual-cyclizative coupling of ynone oxime ethers with acrylamides for the synthesis of isoxazolyl 2-oxindoles. The cascade is triggered by a palladium(ii)-catalyzed ynone oxime ether cyclization, and is completed by a Heck-type coupling.

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38

Zeni, Gilson, Rodrigo Panatieri, Joel Reis, Lysandro Borges, and Cristina Nogueira. "Synthesis of 2-Alkynyl-Tellurophene Derivatives via Palladium-Catalyzed Cross-Coupling." Synlett 2006, no. 18 (2006): 3161–63. http://dx.doi.org/10.1055/s-2006-941593.

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39

Miyake, Garret, Bin Liu, and Chern-Hooi Lim. "Transition-Metal-Free, Visible-Light-Promoted C–S Cross-Coupling through Intermolecular Charge Transfer." Synlett 29, no. 19 (2018): 2449–55. http://dx.doi.org/10.1055/s-0037-1610230.

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C–S cross-couplings are an important class of reactions applied across organic synthesis, materials science, and pharmaceuticals. Several different methodologies have been developed to achieve this significant transformation. However, currently available synthetic procedures significantly rely on transition metals. This article describes historical developments in the field of transition-metal-catalyzed C–S cross-coupling reactions, the development of a visible-light-driven and catalyst-free approach to C–S bond formation, and future outlooks.

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40

Kubota, Koji, Emiru Baba, Tamae Seo, Tatsuo Ishiyama, and Hajime Ito. "Palladium-catalyzed solid-state borylation of aryl halides using mechanochemistry." Beilstein Journal of Organic Chemistry 18 (July 18, 2022): 855–62. http://dx.doi.org/10.3762/bjoc.18.86.

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This study describes the solid-state palladium-catalyzed cross-coupling between aryl halides and bis(pinacolato)diboron using ball milling. The reactions were completed within 10 min for most aryl halides to afford a variety of synthetically useful arylboronates in high yields. Notably, all experimental operations could be performed in air, and did not require the use of large amounts of dry and degassed organic solvents. The utility of this method was further demonstrated by gram-scale synthesis under solvent-free, mechanochemical conditions.

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Chausset-Boissarie, Laëtitia, Nicolas Cheval, and Christian Rolando. "Palladium-Catalyzed Cross-Coupling of Gem-Bromofluoroalkenes with Alkylboronic Acids for the Synthesis of Alkylated Monofluoroalkenes." Molecules 25, no. 23 (2020): 5532. http://dx.doi.org/10.3390/molecules25235532.

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Monofluoroalkenes are versatile fluorinated synthons in organic synthesis, medicinal chemistry and materials science. In light of the importance of alkyl-substituted monofluoroalkenes efficient synthesis of these moieties still represents a synthetic challenge. Herein, we described a mild and efficient methodology to obtain monofluoroalkenes through a stereospecific palladium-catalyzed alkylation of gem-bromofluoroalkenes with primary and strained secondary alkylboronic acids under mild conditions. This novel strategy gives access to a wide range of functionalized tri- and tetrasubstituted mon

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AI-Hassan, Mohammed I. "A Single-Step Synthesis of Tamoxifen Using Palladium-Catalyzed Cross-Coupling." Synthesis 1987, no. 09 (1987): 816–17. http://dx.doi.org/10.1055/s-1987-28084.

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43

Bisz, Elwira, and Michal Szostak. "Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling of Aryl Chlorobenzoates with Alkyl Grignard Reagents." Molecules 25, no. 1 (2020): 230. http://dx.doi.org/10.3390/molecules25010230.

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Aryl benzoates are compounds of high importance in organic synthesis. Herein, we report the iron-catalyzed C(sp2)–C(sp3) Kumada cross-coupling of aryl chlorobenzoates with alkyl Grignard reagents. The method is characterized by the use of environmentally benign and sustainable iron salts for cross-coupling in the catalytic system, employing benign urea ligands in the place of reprotoxic NMP (NMP = N-methyl-2-pyrrolidone). It is notable that high selectivity for the cross-coupling is achieved in the presence of hydrolytically-labile and prone to nucleophilic addition phenolic ester C(acyl)–O bo

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44

Do, Hoang Huy, Saif Ullah, Alexander Villinger, et al. "Palladium-catalyzed synthesis and nucleotide pyrophosphatase inhibition of benzo[4,5]furo[3,2-b]indoles." Beilstein Journal of Organic Chemistry 15 (November 22, 2019): 2830–39. http://dx.doi.org/10.3762/bjoc.15.276.

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A two-step palladium-catalyzed procedure based on Suzuki–Miyaura cross coupling, followed by a double Buchwald–Hartwig reaction, allows for the synthesis of pharmaceutically relevant benzo[4,5]furo[3,2-b]indoles in moderate to very good yield. The synthesized compounds have been analyzed with regard to their inhibitory activity (IC50) of nucleotide pyrophosphatases h-NPP1 and h-NPP3. The activity lies in the nanomolar range. The results were rationalized based on docking studies.

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Rocard, Lou, and Piétrick Hudhomme. "Recent Developments in the Suzuki–Miyaura Reaction Using Nitroarenes as Electrophilic Coupling Reagents." Catalysts 9, no. 3 (2019): 213. http://dx.doi.org/10.3390/catal9030213.

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Palladium-catalyzed cross-coupling reactions are nowadays essential in organic synthesis for the construction of C–C, C–N, C–O, and other C-heteroatom bonds. The 2010 Nobel Prize in Chemistry to Richard F. Heck, Ei-ichi Negishi, and Akira Suzuki was awarded for the discovery of these reactions. These great advances for organic chemists stimulated intense research efforts worldwide dedicated to studying these reactions. Among them, the Suzuki–Miyaura coupling (SMC) reaction, which usually involves an organoboron reagent and an organic halide or triflate in the presence of a base and a palladium

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Denmark, Scott, and Hyung Chi. "Synthesis of 2-Alkenyl-Tethered Anilines." Synthesis 49, no. 13 (2017): 2873–88. http://dx.doi.org/10.1055/s-0036-1589002.

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Three general routes for the synthesis of (E)-2-alkenyl-tethered anilines have been developed. The first route involves a 3-aza-Cope rearrangement of N-allylic anilines in the presence of a Lewis acid. The requisite N-allylic anilines were prepared by the addition of vinylmagnesium reagents to the corresponding aldimines. The second route details a direct cross-metathesis of 2-allylic or 2-homoallylic anilines with styrenes. The third route involves a palladium-catalyzed C–N cross-coupling of aryl halides. Taken together, these three strategies allowed access to the requisite aniline substrate

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Lippa, Rhys A., David J. Battersby, John A. Murphy, and Tim N. Barrett. "Synthesis of Arylethylamines via C(sp3)–C(sp3) Palladium-Catalyzed Cross-Coupling." Journal of Organic Chemistry 86, no. 4 (2021): 3583–604. http://dx.doi.org/10.1021/acs.joc.0c02958.

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Huang, Xian, and Ya-Pin Wang. "Stereoselective Synthesis of 1,3-Enynyl Tellurides by Palladium-Catalyzed Cross-Coupling Reaction." Synthetic Communications 26, no. 16 (1996): 3087–90. http://dx.doi.org/10.1080/00397919608004612.

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Siamaki, Ali R., Daniel A. Black, and Bruce A. Arndtsen. "Palladium-Catalyzed Carbonylative Cross-Coupling with Imines: A Multicomponent Synthesis of Imidazolones." Journal of Organic Chemistry 73, no. 3 (2008): 1135–38. http://dx.doi.org/10.1021/jo701875b.

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Richardson, Chris, Gordon W. Rewcastle, Denton Hoyer, and William A. Denny. "Palladium-Catalyzed Cross-Coupling in the Synthesis of Pyridinyl Boxazomycin C Analogues." Journal of Organic Chemistry 70, no. 18 (2005): 7436–38. http://dx.doi.org/10.1021/jo0510033.

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