A new three-component coupling reaction of benzyne is described that uses two intermolecular carbopalladation reactions to produce 1,2-functionalized benzene derivatives.

Download full-text PDF

Source
http://dx.doi.org/10.1021/ja0615526DOI Listing

Publication Analysis

Top Keywords

three-component coupling
8
intermolecular carbopalladation
8
coupling benzyne
4
benzyne domino
4
domino intermolecular
4
carbopalladation three-component
4
coupling reaction
4
reaction benzyne
4
benzyne described
4
described intermolecular
4

Similar Publications

The synthesis of perfluoroalkylated fullerenes (PFAFs) holds significant importance due to their enhanced molecular stability, increased lipophilicity, and high electron affinity. Herein, we report a copper-catalyzed multicomponent reaction conducted under aerobic conditions, which enables the production of highly soluble PFAFs with half-wave reduction potentials similar to those of C. Furthermore, the challenges posed by C-F coupling in carbon signal assignment were addressed through fluorine-decoupled carbon spectroscopy, facilitating precise structural characterization of the perfluoroalkyl moieties.

View Article and Find Full Text PDF

Multicomponent reactions (MCRs), highly sought-after methods to produce atom-, step-, and energy-economic organic syntheses, have been developed extensively. However, catalytic asymmetric MCRs, especially those involving radical species, remain largely unexplored owing to the difficulty in stereoselectively regulating the extraordinarily high reactivity of open-shell radical species. Herein, we report a conceptually novel catalytic asymmetric three-component radical cascade reaction of readily accessible glycine esters, α-bromo carbonyl compounds and 2-vinylcyclopropyl ketones via synergistic photoredox/Brønsted acid catalysis, in which three sequential C-C (σ/π/σ) bond-forming events occurred through a radical addition/ring-opening/radical-radical coupling protocol, affording an array of valuable enantioenriched unnatural α-amino acid derivatives bearing two contiguous stereogenic centers and an alkene moiety in moderate to good yield with high diastereoselectivity, excellent enantioselectivity and good -dominated geometry under mild reaction conditions.

View Article and Find Full Text PDF

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 PDF

From 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 PDF

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 PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!