Review
Chemistry, Multidisciplinary
Shelesh Krishna Saraswat, Ramanjaneyulu Seemaladinne, Media Noori Abdullah, Halim Zaini, Nabeel Ahmad, Nafis Ahmad, Esmail Vessally
Summary: Aryl fluorosulfates are versatile building blocks in organic synthesis and have gained increasing attention in SuFEx click chemistry. They can be easily prepared from phenols using low-cost sulfuryl fluoride as a sulfonyl fluoride provider. They have been used as less toxic and more atom economical alternatives to triflates in numerous cross-coupling reactions. This review summarizes the recent advances and developments in utilizing aryl fluorosulfates as electrophilic partners in cross-coupling reactions.
Article
Chemistry, Multidisciplinary
Zhenghong Zhou, Jimin Yang, Bo Yang, Yang Han, Lijuan Zhu, Xiao-Song Xue, Feng Zhu
Summary: This study presents a pioneering example of nickel-catalysed enantioconvergent Stille cross-coupling reactions. The reactions result in the formation of C-C bonds in good to high yields with excellent stereoselectivity, providing a practical and cost-effective method for synthesis. The innovative use of synergistic photoredox/nickel catalysis enables a novel single-electron transmetalation process, opening up new research possibilities in the field of Stille reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Multidisciplinary Sciences
Lara E. Zetzsche, Jessica A. Yazarians, Suman Chakrabarty, Meagan E. Hinze, Lauren A. M. Murray, April L. Lukowski, Leo A. Joyce, Alison R. H. Narayan
Summary: This study demonstrates the use of cytochrome P450 enzymes for biocatalytic cross-coupling reactions, enabling the formation of sterically hindered biaryl bonds through oxidative C-C bond formation. By engineering the substrate and atroposelectivity of the P450 enzyme, a highly efficient and selective process has been developed.
Article
Materials Science, Paper & Wood
Pouya Ghamari Kargar, Milad Nayebi, Zahra Parhizi, Rajender S. Varma
Summary: An eco-friendly approach was used to generate Ni nanoparticles on a magnetized cellulose biopolymer, resulting in a core-shell type nanocomposite (Fe3O4@CNF@Ni). The nanocomposite was characterized using various advanced techniques and its catalytic performance was evaluated in the synthesis of biaryl derivatives. The results showed that the nanocomposite exhibited high stability and catalytic efficiency.
Article
Chemistry, Multidisciplinary
Weixu Lu, Xiaoqiang Yu, Ming Bao
Summary: In this paper, a group of copper-based ternary deep eutectic solvents (Cu-DESs) were synthesized and applied in Glaser-type homo- and cross-coupling of terminal alkynes. These reactions occurred under exogenous-ligand-free, base-free, and additive-free conditions, providing satisfactory to excellent yields (up to 99%) under mild conditions. The Cu-DESs can be recycled eight times, with water being the only by-product, complying fully with the principles of green chemistry.
Article
Chemistry, Physical
Elvis N. Nishida, Elder C. Leopoldino, Laize Zaramello, Higor A. Centurion, Renato Goncalves, Ricardo F. Affeldt, Carlos E. M. Campos, Bruno S. Souza
Summary: A novel Pd(II)-polymeric pre-catalyst was successfully prepared and demonstrated good activity in the Suzuki-Miyaura coupling reaction. The catalyst showed recyclability and its performance was affected by the concentration of the cross-coupling partners. The presence of oxygen was found to be crucial in preventing the formation of inactive Pd(0) aggregates.
Article
Chemistry, Multidisciplinary
Yangqing Liu, Jingwen Sun, Lan Fan, Qi Xu
Summary: In this study, new Schiff base-imidazole-functionalized MOFs were synthesized, and highly dispersed Pd clusters showed excellent catalytic activity in the Suzuki coupling reaction with a yield of over 99%.
FRONTIERS IN CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Takanori Iwasaki, Nobuaki Kambe
Summary: Carbon-fluorine bonds are stable but can be selectively transformed under appropriate conditions, making them useful synthetic methods in organic chemistry. This review focuses on C-C bond formation at monofluorinated sp(3)-hybridized carbons via C-F bond cleavage, including cross-coupling and multi-component coupling reactions. The mechanisms of C-F bond cleavage on sp(3)-hybridized carbon centers are categorized into three types: Lewis acids promoted F atom elimination, nucleophilic substitution with metal or carbon nucleophiles, and cleavage of C-F bonds via single electron transfer. Furthermore, the unique characteristics of alkyl fluorides compared to other (pseudo)halides as electrophilic coupling counterparts are discussed.
Article
Chemistry, Inorganic & Nuclear
Nalluchamy Muniyappan, Qazi Mohammad Junaid, Shahulhameed Sabiah
Summary: Several picolyl and benzyl linked biphenyl nickel NHC complexes were synthesized and characterized, and then utilized as catalysts in Suzuki-Miyaura cross-coupling reaction to achieve moderate to good yields of various biphenyls.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2021)
Article
Materials Science, Paper & Wood
Zhian Xu, Jinxi Xu, Waner Zheng, Yiqun Li
Summary: A novel and efficient cellulose-based Pd@Cell-EDTA catalyst was easily prepared through the esterification of cellulose with ethylenediaminetetraacetic dianhydride and subsequent coordination with PdCl2. The Pd@Cell-EDTA catalyst showed excellent activity in Suzuki reactions and Sonogashira reactions, and it could be reused multiple times without significant loss of catalytic performance.
Article
Nanoscience & Nanotechnology
Eadaoin Casey, Justin D. Holmes, Gillian Collins
Summary: This study reports a one-pot synthesis of surfactant templated PdAu nanosheets and investigates their catalytic performance in light-enhanced Suzuki cross coupling reactions. The PdAu bimetallic nanosheets demonstrate higher catalytic activity compared to monometallic Pd nanosheets and commercial Pd/C at room temperature.
ACS APPLIED NANO MATERIALS
(2022)
Review
Chemistry, Multidisciplinary
Fatemeh Mohajer, Majid M. Heravi, Vahideh Zadsirjan, Nargess Poormohammad
Summary: The Sonogashira reaction is a key cross-coupling reaction in organic synthesis, forming a C-C bond between a vinyl or aryl halide and a terminal alkyne. While traditionally requiring copper and phosphines or amines as co-catalysts and bases, recent developments have enabled the reaction to proceed without these components. This advancement could promote the principles of green chemistry and enhance the economic feasibility of the reaction.
Article
Chemistry, Multidisciplinary
Anindita Dewan, Manashi Sarmah, Prantika Bhattacharjee, Pankaj Bharali, Ashim J. Thakur, Utpal Bora
Summary: This study reports the design, synthesis, and application of naturally occurring cellulose from agro waste pomegranate peel as a novel support for active biogenic Pd nanoparticles for Suzuki-Miyaura and Sonogashira cross-coupling reactions at room temperature. The cellulose matrix enables well dispersion of Pd nanoparticles over the support to generate Pd@cellulose, exhibiting excellent catalytic activity and recyclability under ligand-free mild reaction conditions. The synthesized cellulose nanofibers and Pd-anchored heterogeneous nanofibers were characterized through various analytical techniques.
SUSTAINABLE CHEMISTRY AND PHARMACY
(2021)
Review
Chemistry, Inorganic & Nuclear
Radhika Malav, Sriparna Ray
Summary: Carbon-carbon cross coupling reactions are important organic transformations, and various catalysts have been developed for these reactions. Phosphine-based ligands were initially used but were toxic and sensitive. Schiff base ligands, synthesized from condensation reactions, are stable and widely utilized in C-C cross coupling reactions. Palladium complexes are well-known catalysts, but other transition metal complexes are also of interest. This review focuses on the synthesis of Schiff base ligands, their complexation especially with Pd, Co, and Cu, and their application in C-C cross coupling reactions.
INORGANICA CHIMICA ACTA
(2023)
Review
Chemistry, Multidisciplinary
Ahmed H. M. Elwahy, Ismail A. Abdelhamid, Mohamed R. Shaaban
Summary: This research discusses the recent developments in the synthesis of azulene derivatives through Pd-catalyzed coupling techniques over the previous two decades, including various substitution and coupling methods involving different organic groups and reaction conditions.
Article
Engineering, Electrical & Electronic
Stefanie Hildebrandt, Isabel Kinski, Sindy Mosch, Andreas Waltinger, Florian Uhlig, Alexander Michaelis
MICROSYSTEM TECHNOLOGIES-MICRO-AND NANOSYSTEMS-INFORMATION STORAGE AND PROCESSING SYSTEMS
(2015)
