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Homogenous Palladium-Catalyzed Dehalogenative Deuteration and Tritiation of Aryl Halides with D/T Gas.
J Am Chem Soc
November 2024
Process Research & Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States.
Hydrogen isotopically labeled compounds have extensive utility across diverse domains, especially in drug discovery and development. However, synthesis of the labeled compounds with exclusive site selectivity and/or high isotope incorporation is challenging. One widely employed method is heterogeneous palladium(0)-catalyzed (such as Pd/C) dehalogenative deuteration and tritiation with D/T gas.
View Article and Find Full Text PDFPd-Catalyzed Hydrocyanation of Methylenecyclopropanes: A Highly Selective Ring-Opening Access to 2-Substituted Allylic Nitriles.
Org Lett
November 2024
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, 2318 Yuhangtang Road, Hangzhou 311121, China.
Transition-metal-catalyzed hydrofunctionalization of methylenecyclopropanes presents a useful but challenging transformation due to the complex selectivity and multiple reaction pathways. We describe herein an unprecedented highly efficient and selective palladium-catalyzed hydrocyanation of methylenecyclopropanes to give various 2-substituted allylic nitriles. Mechanistic studies demonstrated that the transformation may undergo Markovnikov-type hydrometalation and β-carbon elimination.
View Article and Find Full Text PDFPalladium-Catalyzed Site-Selective Hydrogenation of Unactivated Alkenes Directed by 8-Aminoquinoline Amides.
Chem Pharm Bull (Tokyo)
October 2024
Graduate School of Biomedical and Health Sciences, Hiroshima University.
We have developed a method for the site-selective hydrogenation of unactivated alkenes using 8-aminoquinoline amide as the directing group. For unactivated alkenes with two C-C double bonds, Daugulis's 8-aminoquinoline amide facilitated the site-selective hydrogenation of the desired C-C double bond, producing a product in which one C-C double bond was reduced. Site-selective reduction methodologies using intramolecular directing groups are expected to contribute significantly to the synthesis of molecules with multiple reducible functional groups in the future.
View Article and Find Full Text PDFNIR absorbing ferrocenyl perylenediimide-based donor-acceptor chromophores.
Dalton Trans
September 2024
Department of Chemistry, Indian Institute of Technology Indore (M.P.), 453552, India.
A set of ferrocenyl-functionalized perylenediimide (PDI) compounds and their 1,1,4,4-tetracyanobuta-1,3-diene (TCBD) derivatives 1-5 were designed and synthesized using palladium-catalyzed Sonogashira cross-coupling, followed by a thermally activated [2 + 2] cycloaddition-retroelectrocyclization [CA-RE] reaction with a 1,1,2,2-tetracyanoethylene (TCNE) acceptor in good yields. The TCBD group works as an acceptor, whereas the ferrocenyl group acts as a donor at the central PDI core. The effects of varying the number of ferrocenyl and TCNE groups on the photophysical, thermal, electrochemical, and spectroelectrochemical properties were studied.
View Article and Find Full Text PDFEnantioconvergent synthesis of axially chiral amides enabled by Pd-catalyzed dynamic kinetic asymmetric aminocarbonylation.
Nat Commun
August 2024
Frontiers Science Center for Transformative Molecules, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Zhangjiang Institute for Advanced Study, Shanghai Jiao Tong University, Shanghai, China.
Atropisomeric biaryls bearing carbonyl groups have attracted increasing attention due to their prevalence in diverse bioactive molecules and crucial role as efficient organo-catalysts or ligands in asymmetric transformations. However, their preparation often involves tedious multiple steps, and the direct synthesis via asymmetric carbonylation has scarcely been investigated. Herein, we report an efficient palladium-catalyzed enantioconvergent aminocarbonylation of racemic heterobiaryl triflates with amines via dynamic kinetic asymmetric transformation (DyKAT).
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