ArticleNature communications2016
Radical aryl migration enables diversity-oriented synthesis of structurally diverse medium/macro- or bridged-rings.
Article in Nature communications, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 34 papers.
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Who cites it
34 citing papers in PubMed, 191 citations in OpenAlex.
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- Modular Assembly of Macrocyclic Sulfonamides via Consecutive Cascade Ring Expansion Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Synthesis of the Proposed Structure of Celacarfurine and Analogues Using Sequential Cascade Ring Expansion Reactions.Organic letters · 2026Article
- Copper-Catalyzed 1,2-Diazidation and 1,2-Azidooxygenation of 1,3-Dienes: Three Divergent Protocols Using Zhdankin's Reagent.The Journal of organic chemistry · 2025Article
- Remote difunctionalization of alkenes through a photocatalytically triggered radical clock and α-carbonyl carbocation generation.Communications chemistry · 2025Article
- Modular alkyl growth in amines via the selective insertion of alkynes into C-C bonds.Nature chemistry · 2025Article
- Synthesis and Elaboration of Medium-Sized Ring Building Blocks Prepared via Cascade Ring Expansion Reactions.The Journal of organic chemistry · 2025Article
- Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents.Chemical reviews · 2024Review
- Radical-triggered translocation of C-C double bond and functional group.Nature chemistry · 2024Article
- A Modular Strategy for the Synthesis of Macrocycles and Medium-Sized Rings via Cyclization/Ring Expansion Cascade Reactions.Journal of the American Chemical Society · 2024Article
- Divergent access to 5,6,7-perifused cycles.Nature communications · 2023Article
- Accessing chiral sulfones bearing quaternary carbon stereocenters via photoinduced radical sulfur dioxide insertion and Truce-Smiles rearrangement.Nature communications · 2022Article
- Recent Advances in 1,2-Amino(hetero)arylation of Alkenes.Chemistry, an Asian journal · 2022Review
- Synthesis of medium-ring lactams and macrocyclic peptide mimeticsRSC chemical biology · 2022Article
- Copper-Catalyzed Aminoheteroarylation of Unactivated Alkenes through Distal Heteroaryl Migration.ACS catalysis · 2021Article
- Radical Aryl Migration from Boron to Carbon.Journal of the American Chemical Society · 2021Article
- Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions.Molecules (Basel, Switzerland) · 2021Article
- Copper-catalyzed enantioselective synthesis of bridged bicyclic ketals from 1,1-disubstituted-4-methylene-1,6-hexanediols and related alkenols.Chemical communications (Cambridge, England) · 2021Article
- Evaluating the Viability of Successive Ring-Expansions Based on Amino Acid and Hydroxyacid Side-Chain Insertion.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Anodic oxidation triggered divergent 1,2- and 1,4-group transfer reactions of β-hydroxycarboxylic acids enabled by electrochemical regulation.Chemical science · 2020Article
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Authors and funding
12 authors at 3 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Medium-sized and medium-bridged rings are attractive structural motifs in natural products and therapeutic agents. Due to the unfavourable entropic and/or enthalpic factors with these ring systems, their efficient construction remains a formidable challenge. To address this problem, we herein disclose a radical-based approach for diversity-oriented synthesis of various benzannulated carbon- and heteroatom-containing 8-11(14)-membered ketone libraries. This strategy involves 1,4- or 1,5-aryl migration triggered by radical azidation, trifluoromethylation, phosphonylation, sulfonylation, or perfluoroalkylation of unactivated alkenes followed by intramolecular ring expansion. Demonstration of this method as a highly flexible tool for the construction of 37 synthetically challenging medium-sized and macrocyclic ring scaffolds including bridged rings with diverse functionalities and skeletons is highlighted. Some of these products showed potent inhibitory activity against the cancer cell or derivative of human embryonic kidney line in preliminary biological studies. The mechanism of this novel strategy is investigated by control experiments and DFT calculations.
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