A novel three-component Pd/norbornene cooperative catalysis cascade decarboxylative [2+2+2]/[2+2+3]cyclization of 4-iodoisoquinolin-1(2)-ones and -bromobenzoic acids or 8-bromo-1-naphthoic acid has been developed. The method affords a range of fused phenanthridinones and hepta[1,2-]isoquinolinones and displays unique regioselectivity and broad substrate scope. Palladium/norbornene (Pd/NBE)-catalyzed C-H activation and subsequent decarboxylative coupling reactions were involved, and NBE acts as a building block for the construction of rigid nonplanar molecular architectures.
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http://dx.doi.org/10.1021/acs.joc.3c00344 | DOI Listing |
Org Biomol Chem
January 2025
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310014, P. R. China.
Succinyldiamide derivatives are important structural motifs in various natural products, pharmaceuticals, and functional materials. Herein, a novel, mild, and environmentally friendly method was developed for synthesizing functionalized succinyldiamides each containing a quaternary carbon center. This strategy was designed to involve photocatalytic decarboxylation of readily available oxalic monoamide using a non-precious metal photocatalyst, 4CzIPN, followed by a free-radical addition/Smiles rearrangement cascade reaction of -aryl--(arylsulfonyl)acrylamides.
View Article and Find Full Text PDFOrg Lett
January 2025
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
Chemistry
December 2024
Fraunhofer Institute for Microengineering and Microsystems IMM, Carl-Zeiss-Strasse 18-20, 55129, Mainz, Germany.
The selective decarboxylative fluorination of 3-oxo-3-phenylpropionic acid is used as a benchmark reaction to optimize it under biocompatible conditions in batch and to transfer it to continuous flow mode. The reaction conditions are varied with respect to temperature, fluorinating reagents, inorganic base additives, and pH, as these parameters have been identified as having a significant impact on the process. The formation of the products and any by-products is analyzed using gas chromatography (GC) and F nuclear magnetic resonance spectroscopy (NMR).
View Article and Find Full Text PDFEnviron Sci Technol
December 2024
School of Civil and Environmental Engineering, Cornell University, Ithaca, New York 14853, United States.
Polyfluoroalkyl substances can be biotransformed in natural or engineered environmental systems to generate perfluoroalkyl acids (PFAAs). Data are needed to support the development of biotransformation pathway prediction tools that simulate biotransformation pathways of polyfluoroalkyl substances in specific environmental systems. The goal of this study was to experimentally evaluate the biotransformation of eight structurally similar fluorotelomer acids to identify biotransformation products and propose biotransformation pathways.
View Article and Find Full Text PDFNat Commun
November 2024
Novo Nordisk Research Center Seattle, Inc., Seattle, WA, USA.
C-terminal α-amidated peptides are attractive therapeutic targets, but preparative methods to access amidated pharmaceuticals are limited both on lab and manufacturing-scale. Here we report a straightforward and scalable approach to the C-terminal α-amidation of peptides and proteins from cysteine-extended polypeptide precursors. This amidation protocol consists of three highly efficient steps: 1) selective cysteine thiol substitution with a photolabel, 2) photoinduced decarboxylative elimination and 3) enamide cleavage by simple acidolysis or inverse electron demand Diels-Alder reaction.
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