Activated alkyl halides have been extensively explored to generate alkyl radicals with Ru- and Ir- photocatalysts for 1,2-difunctionalization of alkenes, but unactivated alkyl bromides remain challenging substrates due to their strong reduction potential. Here we report a three-component 1,2-difunctionalization reaction of alkenes, unactivated alkyl bromides and nucleophiles (e.g., amines and indoles) using a trinuclear gold catalyst [Au (tppm) ](OTf) . It can achieve the 1,2-aminoalkylation and 1,2-alkylarylation readily. This protocol has a broad reaction scope and excellent functional group compatibility (>100 examples with up to 96 % yield). It also affords a robust formal [2+2+1] cyclization strategy for the concise construction of pyrrolidine skeletons under mild reaction conditions. Mechanistic studies support an inner-sphere single electron transfer pathway for the successful cleavage of inert C-Br bonds.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/anie.202305121 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Background: Acne is an inflammatory skin disease afflicting the majority of the world's population at some point in their lifetime, and is seen to be chronic in about 50% of cases. Acne leads to significant social withdrawal, depression, and disfiguring scars in many cases. Available treatments are characterized by high rates of relapse, dangerous side effects, and social stigma, which often leads to poor patient compliance and treatment failure.
View Article and Find Full Text PDFCopper-Catalyzed Successive Radical Reactions of Glycine Derivatives.
Org Lett
January 2025
Gansu International Scientific and Technological Cooperation Base of Water-Retention Chemical Functional Materials, Key Laboratory of Eco-Environment-Related Polymer Materials Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, China.
Here, we present a three-component successive radical addition strategy for the preparation of complex noncanonical α-amino acids from easily available glycine derivatives, alkenes, and aryl sulfonium salts via a copper-catalyzed photoredox-neutral catalytic cycle. The utility of this method is further demonstrated by its application in late-stage site-selective modifications of glycine residues in short peptides. It is worth noting that only 1 mol % copper catalyst is required in this reaction, demonstrating high catalytic efficiency.
View Article and Find Full Text PDFMultiple crosslinked, self-healing, and shape-adaptable hydrogel laden with pain-relieving chitosan@borneol nanoparticles for infected burn wound healing.
Theranostics
January 2025
Department of Radiology, Functional and Molecular Imaging Key Lab of Shaanxi Province, Tangdu Hospital, Air Force Medical University, Xi'an, 710038, Shaanxi, China.
Next-generation wound dressings with multiple biological functions hold promise for addressing the complications and pain associated with burn wounds. A hydrogel wound dressing loaded with a pain-relieving drug was developed for treating infected burn wounds. Polyvinyl alcohol chemically grafted with gallic acid (PVA-GA), sodium alginate chemically grafted with 3-aminobenzeneboronic acid (SA-PBA), Zn, and chitosan-coated borneol nanoparticles with anti-inflammatory and pain-relieving activities were combined to afford a nanoparticle-loaded hydrogel with a PVA-GA/Zn/SA-PBA network crosslinked via multiple physicochemical interactions.
View Article and Find Full Text PDFSc-Catalyzed Asymmetric [2 + 2] Annulation of 2-Alkynylnaphthols with Dienes to Access Cyclobutene Frameworks.
Org Lett
January 2025
State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, P. R. China.
Herein, we introduce a scandium-catalyzed synthetic strategy that provides access to a diverse and functionalized array of cyclobutene frameworks adorned with a quaternary carbon center. This approach broadens the synthetic repertoire of 2-alkynylnaphthols with alkenes, offering a versatile platform for the construction of complex molecular architectures. The asymmetric catalytic [2 + 2] cycloaddition reaction demonstrates a wide substrate scope and an impressive functional group tolerance, yielding products with high efficiency, up to 97% yield, and excellent enantiomeric excess of up to 97%.
View Article and Find Full Text PDFFacile Access to Quaternary Carbon Centers via Ni-Catalyzed Arylation of Alkenes with Organoborons.
J Am Chem Soc
January 2025
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. China.
Quaternary carbon centers are widespread structural motifs, thus representing extensive interest in organic synthesis. We describe here an efficient nickel-catalyzed intermolecular, -selective arylation of minimally functionalized alkenes with stable organoborons, affording a broad range of cyclic or acyclic quaternary carbon centers under mild conditions. The utilization of the diimine ligand is critical for high reactivity and chemoselectivity.
View Article and Find Full Text PDFWant 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!