Article
Chemistry, Physical
Juan C. Caravez, Madison J. Wong, Rahul D. Kavthe, Balaram S. Takale, Bruce H. Lipshutz
Summary: Amides, acids, and thioesters can be easily formed from precursor aryl/heteroaryl halides under micellar catalysis conditions using W(CO)(6) as a carbon monoxide source. Palladium catalysts with ligands are usually loaded at around 0.5 mol%. Higher yields were obtained with iodides compared to bromides. Applications in the pharmaceutical industry and examples from the Merck Informer Library are demonstrated. E Factor calculations and options for recycling the aqueous reaction medium are also presented.
Article
Chemistry, Organic
Ruiting Yang, Qiumin Xie, Qian Yan, Xiuli Zhang, Bao Gao
Summary: A novel approach for synthesizing thioesters using S-aryl thioformates as sources was reported, showing smooth transfer of the thioester moiety to aryl iodides. The reaction can be conducted at ambient temperature and tolerates a variety of substrates, with moderate to excellent yields. The scalability of this method was demonstrated through a gram-scale reaction with little change in chemical yield.
Article
Chemistry, Organic
Ruiting Yang, Qiumin Xie, Qian Yan, Xiuli Zhang, Bao Gao
Summary: A novel method for synthesizing thioesters using S-aryl thioformates as sources has been reported. The reaction achieved desirable yields of thioesters with various substrates under mild conditions. Gram-scale synthesis was also successful using this method.
Article
Chemistry, Multidisciplinary
Charles O. Oseghale, Oluwatayo Racheal Onisuru, Dele Peter Fapojuwo, Batsile M. Mogudi, Pule Petrus Molokoane, Nomathamsanqa Prudence Maqunga, Reinout Meijboom
Summary: A novel environmentally friendly green chemical process using a newly developed catalyst was reported, minimizing waste and hazards associated with conventional organic acids and molecular gases. The reaction procedure is facile and milder, achieving moderate to high yields without the need for acid co-catalysts or anhydrides for CO release. The catalyst reusability through scalable, safer, and practical reactions suggests a potential novel method for synthesizing carboxylic acids, amides, and esters.
Article
Chemistry, Multidisciplinary
Lucy van Dijk, Brittany C. Haas, Ngiap-Kie Lim, Kyle Clagg, Jordan J. Dotson, Sean M. Treacy, Katarzyna A. Piechowicz, Vladislav A. Roytman, Haiming Zhang, F. Dean Toste, Scott J. Miller, Francis Gosselin, Matthew S. Sigman
Summary: We report a palladium-catalyzed cross-coupling method for the enantioselective aryl-carbonylation of sulfonimidamides. Data science techniques were employed to guide reaction optimization by sampling the catalyst chemical space. The method offers a general and efficient strategy for accessing enantioenriched sulfonimidamides for medicinal chemistry and agrochemical discovery.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Pui Kin Tony Lo, Michael C. Willis
Summary: This study presents a new redox-neutral Ni(II)-catalyzed reaction system for the addition of (hetero)aryl boroxines to N-sulfinyltritylamine to produce sulfinamide products. The initially formed sulfinamides can be further transformed into various compounds through chlorination and hydrolysis. These transformations can all be conducted through one-pot procedures.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Physical
Ruchita R. Thakore, Balaram S. Takale, Vani Singhania, Fabrice Gallou, Bruce H. Lipshutz
Summary: The new technology enables efficient cyanation reactions of highly complex molecules in water, with significant implications for advancing drug synthesis and discovery.
Article
Chemistry, Multidisciplinary
Fu-Peng Wu, Yang Yuan, Jiawang Liu, Xiao-Feng Wu
Summary: An unprecedented and challenging defluorinative carbonylation reaction was achieved with the first example of defluorinative carbonylative coupling established using a Pd/Cu cooperative catalyst system. This methodology, using gem-difluoroalkenes and aryl iodides as substrates, provides flexible and facile access to privileged alpha-fluorochalcones under mild reaction conditions in moderate-to-excellent yields. Mechanistic studies demonstrated that transmetalation between palladium and copper intermediates is a crucial step in the catalytic cycle.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Shi-Yu Chen, Yu-Hang Song, Shuang Jiao, Chen Zou, Shi-Huan Li, Changle Chen, Xiao-Bing Lu, Ye Liu
Summary: Polyethylenes are widely used synthetic polymers, and introducing functional groups into polyethylene backbone can improve environmental persistence and compatibility with other materials. However, this process is hindered by the formation of alternating polyketones. By reducing the carbonyl density in polyketones, their properties become closer to polyethylene. In this study, Ni and Pd-coordinated cationic catalysts were used for nonalternating carbonylative copolymerization of ethylene, resulting in car-bonyl functionalized polyethylenes with similar properties to commercial high-density polyethylene.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Organic
Vinothkumar Ganesan, Seokyeong Moon, Sungho Yoon
Summary: A phenanthroline-based porous organic polymer supported heterogeneous Pd catalyst (Pd@Phen-POP) was synthesized by solvent knitting using dichloromethane as a linker source in the presence of Lewis acid AlCl3 catalyst for the Friedel-Crafts reaction. The catalyst effectively catalyzes the alkoxycarbonylation of various substituted aryl iodides with diverse alcohols, producing good to excellent yields. Due to its heterotic nature, the catalyst can be easily separated by simple filtration and recycled.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Tania Xavier, Christophe Pichon, Marc Presset, Erwan Le Gall, Sylvie Condon
Summary: The method utilizes palladium catalysis to achieve substitution reactions on coumalates, leading to the synthesis of derivatives with 2-pyran-5-carboxylate groups.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Stefano Paganelli, Riccardo Tassini, Oreste Piccolo
Summary: This paper focuses on the synthesis of important aromatic aldehydes using hydrogen donors and recyclable phosphine free low metal content catalysts, which can be used in industrial flavor/fragrances, API preparation, and other fragrances.
Article
Chemistry, Organic
Christopher S. Gravatt, Jeffrey W. Johannes, Eric R. King, Avipsa Ghosh
Summary: This study presents a method using a stable Ni(II) salt and an iridium photocatalyst for the trifluoromethylthiolation of diverse aryl and heteroaryl iodides. The reaction demonstrates broad functional group tolerance and potential application in medicinal chemistry.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Christopher S. Gravatt, Jeffrey W. Johannes, Eric R. King, Avipsa Ghosh
Summary: This study reports a method using a stable Ni(II) salt and an iridium photocatalyst to mediate the trifluoromethylthiolation of various electronically diverse aryl and heteroaryl iodides. The reaction shows broad functional group tolerance and potential application in medicinal chemistry.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Bijan Mirabi, Austin D. Marchese, Mark Lautens
Summary: In this study, a nickel-catalyzed cross-electrophile coupling reaction of aryl chlorides and heteroaryl chlorides was reported, enabled by a synergistic combination of halide effects and the addition of a magnesium salt. Electronic-deficient aryl chlorides were found to perform the best in the reaction, and preliminary mechanistic evidence showed that MgCl2 is crucial for accelerating the reduction of Ni(II) while small quantities of iodide lead to improved yields.
Article
Pharmacology & Pharmacy
Sphamandla Ntshangase, Adeola Shobo, Hendrik G. Kruger, Arndt Asperger, Dagmar Niemeyer, Per I. Arvidsson, Thavendran Govender, Sooraj Baijnath
Review
Chemistry, Organic
Praveen K. Chinthakindi, Per I. Arvidsson
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Infectious Diseases
Sooraj Baijnath, Chivonne Moodley, Bongani Ngcobo, Sanil D. Singh, Hendrik G. Kruger, Per I. Arvidsson, Tricia Naicker, Alexander Pym, Thavendran Govender
INTERNATIONAL JOURNAL OF ANTIMICROBIAL AGENTS
(2018)
Article
Chemistry, Organic
Praveen K. Chinthakindi, Andrea Benediktsdottir, Ayah Ibrahim, Atta Wared, Carl-Johan Aurell, Anna Pettersen, Edouard Zamaratski, Per I. Arvidsson, Yantao Chen, Anja Sandstrom
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Medicinal
Niranjan Thota, Parameshwar Makam, Kamal K. Rajbongshi, Savania Nagiah, Naeem Sheik Abdul, Anil A. Chuturgoon, Amit Kaushik, Gyanu Lamichhane, Anou M. Somboro, Hendrik G. Kruger, Thavendran Govender, Tricia Naicker, Per I. Arvidsson
ACS MEDICINAL CHEMISTRY LETTERS
(2019)
Article
Chemistry, Organic
Praveen K. Chinthakindi, Andrea Benediktsdottir, Per I. Arvidsson, Yantao Chen, Anja Sandstrom
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Kamal K. Rajbongshi, Srinivas Ambala, Thavendran Govender, Hendrik G. Kruger, Per Arvidsson, Tricia Naicker
SYNTHESIS-STUTTGART
(2020)
Article
Biochemistry & Molecular Biology
Amir Ata Saei, Hjalmar Gullberg, Pierre Sabatier, Christian M. Beusch, Katarina Johansson, Bo Lundgren, Per Arvidsson, Elias S. J. Arner, Roman A. Zubarev
Article
Chemistry, Multidisciplinary
Hlengekile Lubanyana, Per Arvidsson, Thavendran Govender, Hendrik G. Kruger, Tricia Naicker
Review
Chemistry, Medicinal
Nakita Reddy, Mbongeni Shungube, Per Arvidsson, Sooraj Baijnath, Hendrik G. Kruger, Thavendran Govender, Tricia Naicker
EXPERT OPINION ON THERAPEUTIC PATENTS
(2020)
Article
Clinical Neurology
Karl E. Carlstrom, Praveen K. Chinthakindi, Belen Espinosa, Faiez Al Nimer, Elias S. J. Arner, Per Arvidsson, Fredrik Piehl, Katarina Johansson
Correction
Chemistry, Multidisciplinary
Hlengekile Lubanyana, Per I. Arvidsson, Thavendran Govender, Hendrik G. Kruger, Tricia Naicker
Article
Chemistry, Organic
Lloyd C. Chetty, Hendrik G. Kruger, Per Arvidsson, Tricia Naicker, Thavendran Govender
Summary: A simple method for the direct carboxylation of resorcinols, phenols, and indoles has been reported. The use of supercritical carbon dioxide as an electrophile and solvent under basic conditions yields moderate to high amounts of products. This method eliminates the need for solvents and metals, and avoids the cumbersome exclusion of air or water.
SYNTHESIS-STUTTGART
(2022)
Meeting Abstract
Pharmacology & Pharmacy
Christopher Southan, Per Arvidsson
BRITISH JOURNAL OF PHARMACOLOGY
(2020)
Article
Chemistry, Multidisciplinary
Mzilikazi F. Khumalo, Ekemini D. Akpan, Praveen K. Chinthakindi, Edikarlos M. Brasil, Kamal K. Rajbongshi, Maya M. Makatini, Thavendran Govender, Hendrik G. Kruger, Tricia Naicker, Per I. Arvidsson