ArticlePrecision chemistry2023
Chlorine Atom Transfer of Unactivated Alkyl Chlorides Enabled by Zirconocene and Photoredox Catalysis.
Article in Precision chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Catalytic C-S bond cleavage of simple sulfides with productive retention of thiol fragments.Chemical science · 2026Article
- Zirconocene(III) in Organic Synthesis: Does the Ugly Duckling Become a Swan?International journal of molecular sciences · 2026Review
- Advances in Zr-mediated radical transformations and applications to total synthesis.Beilstein journal of organic chemistry · 2026Review
- Catalytic Reductive Homocoupling of Benzyl Chlorides Enabled by Zirconocene and Photoredox Catalysis.Precision chemistry · 2025Article
- Concise Synthesis of Cyctetryptomycin A and B Enabled by Zr-Catalyzed Dimerization.Angewandte Chemie (International ed. in English) · 2025Article
- Radical Replacement Process for Ligated Boryl Radical-Mediated Activation of Unactivated Alkyl Chlorides for C(spJournal of the American Chemical Society · 2024Article
- Dinuclear gold-catalyzed divergent dechlorinative radical borylation of gem-dichloroalkanes.Nature communications · 2024Article
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Alkyl chlorides are robust precursors to carbon radicals; however, their relative inertness has hampered their practical use. Although modern photochemical strategies have greatly enhanced the utility of alkyl chlorides as radical precursors, these methods often depend on strongly reducing conditions leading to unproductive side reactions. Here, we report a catalytic radical generation from 1°, 2°, and 3° unactivated alkyl chlorides with zirconocene and photoredox catalysis, which enables both hydrogenation and borylation on a range of structurally complex molecules. This mild zirconocene-catalyzed protocol shows that zirconium can render the C-Cl bond cleavage more exergonic and can lower the activation energy of the transition state, amplifying the ability of metallocenes toward halogen atom transfer.
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