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Length and Sequence-Selective Polymer Synthesis Templated by a Combination of Covalent and Noncovalent Base-Pairing Interactions.
J Am Chem Soc
November 2024
Yusuf Hamied Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, U.K.
Information can be encoded and stored in sequences of monomer units organized in linear synthetic polymers. Replication of sequence information is of fundamental importance in biology; however, it represents a challenge for synthetic polymer chemistry. A combination of covalent and noncovalent base pairs has been used to achieve high-fidelity templated synthesis of synthetic polymers that encode information as a sequence of different side-chain recognition units.
View Article and Find Full Text PDFCopper-Catalyzed Hydroamination of 2-Alkynylazobenzenes: Synthesis of 3-Alkenyl-2-Indazoles.
J Org Chem
November 2024
Departamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Andrés M. del Río (IQAR), Facultad de Farmacia, Universidad de Alcalá, Alcalá de Henares, 28805 Madrid, Spain.
A copper-catalyzed intramolecular synthesis of 3-alkenyl-2-indazoles from 2-alkynylazobenzenes is described. The reaction proceeds in a single step via C-N bond formation and a subsequent 1,2-hydride shift, affording products in high yields. DFT calculations suggest the 1,2-hydride shift as the rate-determining step.
View Article and Find Full Text PDFRecent Developments in Copper-Catalyzed Annulations for Synthesis of Spirooxindoles.
Chem Rec
November 2024
College of Advanced Interdisciplinary Science and Technology (CAIST), Henan University of Technology, Zhengzhou, 450001, China.
Spirooxindoles represent a special scaffold for pharmaceuticals and natural products, and significant advancements have been achieved in their synthesis in recent years. Among these, transition metal catalysis, particularly copper catalysis, has emerged as an efficient and reliable method for the synthesis of spirooxindoles. Based on different reaction types, two distinct substrate types have been summarized and classified by us for constructing spirooxindole scaffolds via intramolecular and intermolecular annulations.
View Article and Find Full Text PDFCopper-Catalyzed [3 + 2] Annulation of -Acyl Oximes with -Hydroquinones for the Synthesis of 5-Hydroxyindoles.
J Org Chem
October 2024
School of Petrochemical Engineering, Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, Changzhou University, Changzhou, Jiangsu 213164, China.
A copper-catalyzed [3 + 2] annulation of -acyl oximes with 2-electron-withdrawing group substituted -hydroquinones for the efficient synthesis of polysubstituted 5-hydroxyindoles is developed. Further intramolecular cyclization leads to the concise and rapid construction of several kinds of 3,4- and 4,5-fused polycyclic indoles.
View Article and Find Full Text PDFCopper-Catalyzed Oxidative Synthesis of 3-Aryl-5-fluoroalkyl-1,3,4-oxadiazol-2(3)-ones Using Perfluorocarboxylic Anhydride as a Reagent.
J Org Chem
October 2024
Fujian Provincial University Engineering Research Center of Green Materials and Chemical Engineering, and Fujian Engineering Research Center of New Chinese lacquer Material, College of Materials and Chemical Engineering, Minjiang University, Fuzhou 350108, China.
A copper-catalyzed oxidative annulation of sydnones with perfluorocarboxylic anhydride for the synthesis of 3-aryl-5-fluoroalkyl-1,3,4-oxadiazol-2(3)-ones is developed. A diverse array of 3-aryl-5-fluoroalkyl-1,3,4-oxadiazol-2(3)-ones are prepared with good yields (>73 examples, yields up to 95%). The synthetic utility of the developed protocol was demonstrated by gram-scale synthesis, and the synthetic transformation to 1,2,4-triazol-3-one products.
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