Two photo-catalytic tandem alkyl radical addition/semipinacol rearrangement reactions of cycloalkanol-substituted styrenes with N-acyloxyphthalimides and O-acyl oximes have been documented. These protocols provide efficient access to functionalized cyclic ketones, and feature mild conditions (i.e., visible light irradiation, redox neutral and room temperature), broad substrate scope and excellent functional group tolerance.
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http://dx.doi.org/10.1039/c8cc04503h | DOI Listing |
Chem Sci
December 2024
Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, College of Chemistry and Chemical Engineering, Hubei University Wuhan 430062 P. R. China
The prevalence of naphthalene compounds in biologically active natural products, organic ligands and approved drugs has motivated investigators to develop efficient strategies for their selective synthesis. C-H functionalization of naphthalene has been frequently deployed, but mainly involves two-component reactions, while multiple-component C-H functionalization for the synthesis of naphthalene compounds has thus far proven elusive. Herein, we disclose a versatile three-component protocol for the modular synthesis of multifunctional naphthalenes from readily available simple naphthalenes, olefins and alkyl bromides P(iii)-assisted ruthenium-catalyzed remote C-H functionalization.
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January 2025
Dept. of Chemical Engineering, McGill University 3610 Rue Universite Montreal QC H3A 0C5 Canada
Compositions of ethylene glycol dicyclopentenyl ether methacrylate (EGDEMA), a vegetable oil based alkyl methacrylate (C13MA), and furfuryl methacrylate (FMA) were terpolymerized for dual-crosslinked networks with tailored mechanical and thermal properties. Specifically, initiators for continuous activator regeneration (ICAR) atom transfer radical polymerization (ATRP) afforded materials with tailored glass transition temperature ( ) and incorporation of furan and norbornene functionalities within a single chain. The terpolymer with high furan and norbornene functionality (Ter2: = 0.
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April 2024
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, United States.
We disclose a catalytic photoredox carbobromination of unactivated alkenes with α-bromocarbonyl compounds under a blue LED light. The reaction proceeds with α-bromoesters, α-bromonitriles and α-bromo-γ-lactones along with terminal and 1,2-disubstituted internal alkenes. Reactions with indenes and 1,1-disubstituted alkenes generate alkylated alkenes.
View Article and Find Full Text PDFNat Chem
January 2025
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA, USA.
In view of the high propensity of tertiary alkyl amines to be bioactive, the development of new methods for their synthesis is an important challenge. Transition-metal catalysis has the potential to greatly expand the scope of nucleophilic substitution reactions of alkyl electrophiles; unfortunately, in the case of alkyl amines as nucleophiles, only one success has been described so far: the selective mono-alkylation of primary amines to form secondary amines. Here, using photoinduced copper catalysis, we report the synthesis of tertiary alkyl amines from secondary amines and unactivated alkyl electrophiles, two readily available coupling partners.
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January 2025
Department of Chemistry, Scripps Research, La Jolla, CA, USA.
Amino alcohols are vital in natural products, pharmaceuticals and agrochemicals, and as key building blocks for various applications. Traditional synthesis methods often rely on polar bond retrosynthetic analysis, requiring extensive protecting group manipulations that complicate direct access. Here we show a streamlined approach using a serine-derived chiral carboxylic acid in stereoselective electrocatalytic decarboxylative transformations, enabling efficient access to enantiopure amino alcohols.
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