Article
Chemistry, Multidisciplinary
Sheng-Qi Qiu, Yu Chen, Xiang-Jun Peng, Shi-Jiang He, Jun Kee Cheng, Yong-Bin Wang, Shao-Hua Xiang, Jun Song, Peiyuan Yu, Junmin Zhang, Bin Tan
Summary: In this study, we achieved the arene-alkene Suzuki-Miyaura coupling reaction between hindered aryl halides and vinyl boronates by designing appropriate ligands and reaction parameters. The axially chiral acyclic aryl-alkenes obtained exhibited remarkable efficiency, enantioselectivity, and E/Z selectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Antonio J. LaPorte, Yao Shi, Jason E. Hein, Martin D. Burke
Summary: Stereospecific Csp(3) Suzuki-Miyaura cross-coupling simplifies the synthesis of stereochemically complex small molecules, but current methods are not compatible with complex building blocks commonly found in natural products and other complex targets. This study presents a method for embedding the alpha-methyl-beta-hydroxyl motif within stereochemically defined secondary alkyl boronic ester building blocks, allowing for stereospecific cross-coupling. The use of beta-aryloxysilyl groups addresses the decrease in reactivity and side reactions associated with beta-oxygen-containing Csp(3) boronic esters. Mechanistic studies reveal the activation of a dihydroxysiloxaborolate as a transmetalation partner in a stereospecific process that retains configuration.
Article
Chemistry, Physical
Chau Ming So, On Ying Yuen, Shan Shan Ng, Zicong Chen
Summary: This study presents a general chemoselective Suzuki-Miyaura coupling using a Pd/L33 catalyst, showing efficient coupling of polyhalogenated aryl triflates by controlling reactivity order and key factors, achieving high yields and chemoselectivity with low Pd catalyst loading.
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
Chemistry, Multidisciplinary
Matteo Albino, Thomas J. Burden, Carmen C. Piras, Adrian C. Whitwood, Ian J. S. Fairlamb, David K. Smith
Summary: The increase in demand and low abundance of palladium pose a significant threat to its future availability, making research into sustainable palladium-based technologies crucial. This study reports the development of Pd scavenging hybrid gel beads composed of agarose and a low-molecular-weight gelator based on DBS-CONHNH2. These mechanically robust gel beads exhibit potential as practical catalysts for Suzuki-Miyaura cross-coupling reactions, demonstrating good reusability, green metrics, and improved reaction times compared to previous examples. The leaching of palladium is almost completely eliminated and a detailed investigation explains how the nanoparticles are formed in situ. These ligand-free gel beads can be considered as robust nonligated heterogeneous PdNP catalysts with potential for the development of easily used chemical reaction systems.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Organic
Yanxin Jiang, Kwai Wun Cheng, Haoyang Zhang, Zhiping Yang, Jun Wang
Summary: A new palladium-catalyzed asymmetric Suzuki-Miyaura coupling is demonstrated using a unique monophosphine ligand, Azaphos. This method offers a novel ligand framework for the synthesis of axially chiral compounds via asymmetric Suzuki-Miyaura coupling reactions.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Physical
Yiyang Zhang, Hong Sun, Yonghuai Yang, Haofei Li, Yaocheng Shi, Lei Yu
Summary: The catalytic activities of palladium nanoparticles on a polyaniline support were improved by tungsten doping, resulting in a significantly increased catalyst turnover number (>10(4)) for the Suzuki-Miyaura coupling reaction. Characterization of the materials showed that tungsten doping improved the micro-morphology, leading to more efficient absorption of reactants. Additionally, tungsten facilitated stabilization of Pd(0) species and the transmetallation step, both crucial for the catalytic reaction. Therefore, Pd/W@PANI engineering material may serve as a highly efficient heterogeneous catalyst in the pharmaceutical industry.
CATALYSIS SCIENCE & TECHNOLOGY
(2023)
Article
Chemistry, Applied
Mingyang Gao, Jiamin Wang, Weixiang Shang, Yuchao Chai, Weili Dai, Guangjun Wu, Naijia Guan, Landong Li
Summary: Suzuki-Miyaura cross-coupling reaction is a powerful method to construct carbon-carbon bonds and is widely used in the synthesis of functional organic compounds. In this study, zeolite-encased Pd particles (Pd@MFI) were successfully prepared and investigated as promising heterogeneous catalysts for the Suzuki-Miyaura cross-coupling reaction. The Pd@MFI catalysts showed high activity, with dispersed Pd particles efficiently stabilized within the MFI zeolite matrix. The presence of basic sites adjacent to Pd sites was crucial for achieving high catalytic activity.
Article
Chemistry, Multidisciplinary
Julius Hoepfner, Marius Brehm, Pavel A. Levkin
Summary: The rising costs of pharmaceutical research are currently limiting the productivity of drug discovery and development, but can potentially be reduced through miniaturization of compound synthesis and screening. In this study, the influential palladium-catalyzed Suzuki-Miyaura reaction is successfully implemented at the nanoliter scale on droplet microarrays for the synthesis of an 800-compound library of biphenyls. The synthesis of these compounds requires minimal reagents and solvent volume, and the obtained compounds can be purified and cleaved from excess reactants and catalyst. This novel approach expands the capabilities of droplet microarrays for miniaturized high-throughput chemical synthesis and opens up possibilities for future synthesis and screening of chemical compounds in a single platform.
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
Hamed M. Alshammari, Obaid F. Aldosari, Mohammad Hayal Alotaibi, Raja L. Alotaibi, Mosaed S. Alhumaimess, Moataz H. Morad, Syed Farooq Adil, Mohammed Rafi Shaik, Mohammad Shahidul Islam, Mujeeb Khan, Abdulrahman Alwarthan
Summary: Pd/C catalysts on activated carbon with varying palladium content showed high catalytic activity for Suzuki-Miyaura coupling reactions and Mizoroki-Heck cross-coupling reactions. The catalyst with 3% Pd/C demonstrated better efficiency and reusability compared to other synthesized catalysts, indicating the significance of high 'Pd' content and uniform impregnation on the catalyst activity.
APPLIED SCIENCES-BASEL
(2021)
Article
Chemistry, Applied
Maryam Mohammadikish, Nazanin Mosleh
Summary: Utilizing sunlight as a driving force in chemical reactions is beneficial for sustainability. This study reports the synthesis of a graphitic-carbon nitride system modified with Pd nanoparticles, which exhibits prominent photocatalytic performance for Suzuki-Miyaura coupling reactions.
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
Article
Polymer Science
Chisa Takahara, Masashi Nakamura, Yuto Aoyama, Takumi Yanagihara, Shunichiro Ito, Kazuo Tanaka, Hiroaki Imoto, Kensuke Naka
Summary: Arsenic-containing conjugated polymers have gained significant attention recently. To improve solubility in organic solvents, long alkyl chains are commonly introduced on the coupling partner and/or at the 3-positions of fused thiophene rings in traditional polymer design. However, this strategy is not applicable for comonomers with difficulties in alkyl group substitution, and the steric hindrance of alkyl chains can distort the planarity of polymer chains. Therefore, a novel monomer with an alkoxyphenyl group substituted on the arsenic atom was developed. By using benzothiadiazole and benzoxadiazole monomers, polymers with high planarity and solubility were developed, exhibiting near-infrared emissions.
Article
Polymer Science
Chisa Takahara, Masashi Nakamura, Yuto Aoyama, Takumi Yanagihara, Shunichiro Ito, Kazuo Tanaka, Hiroaki Imoto, Kensuke Naka
Summary: Arsenic-containing conjugated polymers, with dithieno[3,2-b:2',3'-d]arsole as a typical monomer unit, have gained significant attention recently. However, the traditional polymer design for improved solubility often involves introducing long alkyl chains, which may lead to steric hindrance and distort the planarity of the polymer chain. To overcome this, a novel monomer with an alkoxyphenyl group substituted on the arsenic atom was developed. These polymers, using benzothiadiazole and benzoxadiazole monomers, exhibited high planarity and solubility, as well as near-infrared emissions.
Article
Chemistry, Physical
Matthew J. Andrews, Sebastian Brunen, Ruaraidh D. McIntosh, Stephen M. Mansell
Summary: This paper describes the synthesis and catalytic testing of a palladium complex with a 5-membered chelating [N,O] ligand, derived from the condensation of 2,6-diisopropylphenyl aniline and maple lactone. The catalyst was active towards the Suzuki-Miyaura cross-coupling reaction, and its activity was optimised through the selection of base, solvent, catalytic loading and temperature. The catalyst exhibited good activity towards aryl bromides with electron-withdrawing groups, as well as a range of boronic acids and pinacol esters. It was also a capable catalyst for the cross-coupling of aryl chlorides and phenylboronic acid.
Article
Chemistry, Physical
Vincent Fernandez, Daniyal Kiani, Neal Fairley, Francois-Xavier Felpin, Jonas Baltrusaitis
APPLIED SURFACE SCIENCE
(2020)
Article
Chemistry, Applied
Ehu Camille Aka, Eric Wimmer, Elvina Barre, Daniel Cortes-Borda, Tchirioua Ekou, Lynda Ekou, Mireia Rodriguez-Zubiri, Francois-Xavier Felpin
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2020)
Article
Chemistry, Applied
Florian Carpentier, Francois-Xavier Felpin, Francoise Zammattio, Erwan Le Grognec
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2020)
Article
Chemistry, Physical
Junjin Che, Wilfrid Neri, Isabelle Ly, Philippe Poulin, Cecile Zakri, Jinkai Yuan
ACS APPLIED ENERGY MATERIALS
(2020)
Article
Chemistry, Physical
Shrikant Kunjir, Mireia Rodriguez-Zubiri, Vincent Coeffard, Francois-Xavier Felpin, Patrick Giraudeau, Jonathan Farjon
Article
Chemistry, Applied
N. Vasudevan, Eric Wimmer, Elvina Barre, Daniel Cortes-Borda, Mireia Rodriguez-Zubiri, Francois-Xavier Felpin
Summary: This article presents a continuous-flow strategy for the palladium-catalyzed direct C-H arylation of indole-3-acetic acid derivatives with arenediazonium salts, optimizing the coupling reaction in a three-dimensional space using a fully autonomous self-optimizing flow platform. The developed flow methodology is experimentally simple, mild, broad in scope, and safer than traditional batch approaches, particularly suitable for preparing precursors of pharmaceutically relevant compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Materials Science, Multidisciplinary
Marie Denis, Denis Gindre, Francois-Xavier Felpin
Summary: Cyclopropenone derivatives are used as latent photo-released strained cyclic alkynes for covalent printing complex patterns on cellulose paper. The use of a simple UV LED allows quick printing at room temperature with good resolution at the micrometer scale and minimal diffusion. The strategy is proven effective through the sequential printing of a QR code and logo on the same paper sheet.
JOURNAL OF MATERIALS SCIENCE
(2021)
Article
Nanoscience & Nanotechnology
Ali Rouhollah Jalili, Alexandra Satalov, Sahar Nazari, Bryan Harry Rahmat Suryanto, Jing Sun, Mohammad Bagher Ghasemian, Mohannad Mayyas, Ahmad E. Kandjani, Ylias M. Sabri, Edwin Mayes, Suresh K. Bhargava, Jun Araki, Cecile Zakri, Philippe Poulin, Dorna Esrafilzadeh, Rose Amal
Summary: The study demonstrates how liquid crystal ink can be used in 3D printing to bridge the gap between nano- and microscales, enabling intricate patterns within architecturally layered systems. This approach allows for the development of high-performance devices with nanoscopic arrangements in macroscopic printed architectures.
ACS APPLIED MATERIALS & INTERFACES
(2021)
Article
Chemistry, Organic
Aline Makhloutah, Danylo Hatych, Thomas Chartier, Lou Rocard, Antoine Goujon, Francois-Xavier Felpin, Pietrick Hudhomme
Summary: An unprecedented palladium-catalyzed cross-coupling reaction has been reported, allowing for the grafting of aryls in the bay region of PDIs with high selectivity. This reaction has been optimized and successfully applied for the desymmetrization of dinitro-PDI substrates.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Bi Bali Judicael Tra, Abolle Abolle, Vincent Coeffard, Francois-Xavier Felpin
Summary: This paper presents a divergent continuous-flow approach for the biomimetic oxidative cyclization of reticuline-type alkaloids to aporphine and morphinandienone natural products using hypervalent iodine(III) reagents. The method allows for the selective synthesis of target products based on detailed knowledge of the reaction mechanisms, providing robust conditions for the preparation of natural products.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Applied
Mireia Rodriguez-Zubiri, Francois-Xavier Felpin
Summary: The concept and practices of chemical synthesis are transforming towards fully autonomous continuous processes, which require efficient monitoring and online analysis. This review presents the main in-line/online analytical tools for monitoring chemical reactions, serving as a guide for synthetic chemists.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Chemistry, Multidisciplinary
Kouakou Eric Konan, Abolle Abolle, Elvina Barre, Ehu Camille Aka, Vincent Coeffard, Francois-Xavier Felpin
Summary: Continuous flow photo-thiol-ene reactions on cinchona alkaloids with a variety of organic thiols have been developed to deliver a series of unprecedented architectures. A self-optimizing flow photochemical reactor was used to identify the optimal experimental conditions. The flow thiol-ene reaction proceeds under mild conditions, maximizing photon absorption and increasing reaction rates and yields compared to traditional batch reactors.
REACTION CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Multidisciplinary
N. Vasudevan, Ehu C. Aka, Elvina Barre, Eric Wimmer, Daniel Cortes-Borda, Patrick Giraudeau, Jonathan Farjon, Mireia Rodriguez-Zubiri, Francois-Xavier Felpin
Summary: This study presents a straightforward continuous flow synthesis of FGIN-1-27, a compound with potent anxiolytic effects, from inexpensive and commercially available starting materials. The four-step synthesis includes the direct C-H arylation of an indole with an arenediazonium salt. The use of enabling technologies such as real-time in-line benchtop F-19 NMR analysis and an optimization algorithm improves process safety and reduces the number of experiments needed in optimization campaigns.
REACTION CHEMISTRY & ENGINEERING
(2021)
Meeting Abstract
Gastroenterology & Hepatology
Adeline Sivignon, Antoine Chaprenet, Francois-Xavier Felpin, Julie Bouckaert, Sebastien G. Gouin, Nicolas Barnich
Article
Multidisciplinary Sciences
Jinkai Yuan, Wilfrid Neri, Cecile Zakri, Pascal Merzeau, Karl Kratz, Andreas Lendlein, Philippe Poulin
