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Photocatalytic Three-Component Reductive Coupling Synthesis of -Difluorohomoallyl Secondary Amines.
J Org Chem
January 2025
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Sciences, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, P. R. China.
-Difluorohomoallyl amines, an important class of -difluoroalkenes, are prevalent moieties in many bioactive compounds. However, limited methods are suitable for the synthesis of this type of compound containing secondary amines. Here, we display a photocatalytic multicomponent protocol for the synthesis of -difluoroalkenes containing secondary amines, which makes use of readily available materials: arylamines, alkyl aldehydes, and α-trifluoromethyl alkenes.
View Article and Find Full Text PDFFrom Radical Coupling to Enantioselective Controlled Protonation: Advancing Precise Construction of Stereocenters.
J Am Chem Soc
January 2025
Henan Key Laboratory of Natural Medicine Innovation and Transformation, Henan University, Kaifeng, Henan 475004, PR China.
Recent advancements in green and sustainable platforms, particularly visible light-driven photocatalysis, have spurred significant progress in radical chemistry, enabling the efficient synthesis of important molecules from simple and readily available feedstocks under mild conditions. However, the rapid orbital flipping and high reactivity of radicals pose substantial challenges for achieving precise enantiocontrol in stereocenter formation via radical coupling. In this study, we present a generic and efficient strategy that modulates this elusive approach, facilitating enantiocontrollable protonation through 1,3-boron migration.
View Article and Find Full Text PDFIdentification of Components of the Sex Pheromone of the kōwhai Moth, Uresiphita Polygonalis Maorialis, a New Zealand Native Crambid.
J Chem Ecol
January 2025
Canterbury Research Centre, The New Zealand Institute for Plant and Food Research Limited, Lincoln, 8152, New Zealand.
The identification of sex pheromones in native New Zealand moths has been limited, largely due to their minimal pest impact on agricultural ecosystems. The kōwhai moth, Uresiphita polygonalis maorialis, a native crambid, is known for its herbivory on Sophora spp. and Lupinus arboreus leaves.
View Article and Find Full Text PDFPhotoredox-Enabled Direct and Three-Component Difluoroalkylative Modification of -Aryl Glycinates.
Org Lett
January 2025
Hubei Key Laboratory of Bioinorganic Chemistry & Materia Medica, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan, Hubei 430074, China.
A Cu(I) photoredox-enabled reaction that selectively incorporates a difluoroalkyl group into -aryl glycine derivatives has been established. Using a bench-stable [PhPCFH]Br salt, the -CFH group could be installed either directly on the α-carbon of the glycine backbone or in a three-component fashion using an alkene as a bridge. A series of glycine derivatives have been evaluated, providing access to diverse unnatural amino esters and dipeptides with a -CHF unit.
View Article and Find Full Text PDFPhotoredox cobalt dual catalysis toward C3-functionalization of quinoxalinones with alkenes and alkynes.
Chem Commun (Camb)
January 2025
Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, Tamil Nadu, India.
A site-selective coupling involving quinoxalin-2-ones with alkenes and alkynes has been developed through synergistic visible-light photoredox cobalt catalysis. This method enables C3-selective alkylation and alkenylation of both -substituted and -unsubstituted quinoxalin-2-ones, achieving high yields under mild conditions. Of note, the protocol facilitates the incorporation of two alkene units, leading to a formal three-component coupling, whereas a two-component coupling is preferred for alkynes.
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