ArticleChemical reviews2019
Mechanistic Aspects and Synthetic Applications of Radical Additions to Allenes.
Article in Chemical reviews, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 37 papers.
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Who cites it
37 citing papers in PubMed, 241 citations in OpenAlex.
- Electrochemically Driven Regioselective Radical Functionalization of Allenes: Scope and Mechanistic Insights.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Iron-Catalyzed Cyclopropanation of Allenes Using Unactivated Alkyl Sulfonium Salts.Angewandte Chemie (International ed. in English) · 2026Article
- Diverse radical transformations of allenic C(sp)-C(spNature communications · 2026Article
- Programmable Functionalizations of Tetramethylpiperidine N-Oxyl (TEMPO)-Acrolein Linchpins Derived from Alkoxyallenes.Journal of the American Chemical Society · 2026Article
- Alcohol-Directed Carboamination of Conjugated Enynes.Angewandte Chemie (International ed. in English) · 2026Article
- All About the Base: Electrochemical Isomerization of Terminal Propargyl Compounds toward the Synthesis of Allenes and Phenols.Organic letters · 2026Article
- Visible-Light Mediated Activation of 1,3-Dienes and Allenes via Energy Transfers.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Enantioconvergent Cobalt-Catalyzed Hydroalkylation for the Construction of Fluoro, Chloro, and Trifluoromethyl Stereogenic Centers.Angewandte Chemie (International ed. in English) · 2025Article
- Copper-Mediated Divergent Reactivity of Allene-Tethered Carbamates under Radical Conditions.Organic letters · 2025Article
- Electrochemical synthesis of allenyl silanes and allenyl boronic esters.Nature communications · 2025Article
- Stereoselective rhodium-catalyzed reaction of allenes with organoboronic reagents for diversified branched 1,3-alkadienes.Nature communications · 2024Article
- Copper-catalyzed remote double functionalization of allenynes.Chemical science · 2024Article
- Kinetic and reactivity of gas-phase reaction of acyclic dienes with hydroxyl radical in the 273-318 K temperature range.RSC advances · 2024Article
- Cross-coupling of organic fluorides with allenes: a silyl-radical-relay pathway for the construction of α-alkynyl-substituted all-carbon quaternary centres.Chemical science · 2024Article
- Recent Progress in Free Radical Transformations of Allenamides.Current organic synthesis · 2024Article
- Multicomponent Reactions between Heteroatom Compounds and Unsaturated Compounds in Radical Reactions.Molecules (Basel, Switzerland) · 2023Review
- A Pd-catalyzed highly selective three-component protocol for trisubstituted allenes.Chemical science · 2023Article
- Article
- Synthesis of N-, O-, and S-heterocycles from aryl/alkyl alkynyl aldehydes.RSC advances · 2023Review
- Metal-Free One-Pot Multi-Functionalization of Unsaturated Compounds with Interelement Compounds by Radical Process.Molecules (Basel, Switzerland) · 2023Review
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
More than 50 years have passed since Haszeldine reported the first addition of a trifluoromethyl radical to an allene; in the intervening years, both the chemistry of allenes and the reactivity of single-electron species have become topics of intense interest. In this Review, we provide an overview of the fundamentals of radical additions to allenes and highlight the emergence of theoretical and experimental evidence that reveals unique reactivity patterns for radical additions to allenes as compared with other unsaturated compounds. Factors capable of exerting control over the chemo-, regio-, and stereoselectivities of the attack of carbon- and heteroatom-based radicals at each of the three potential reactive sites in an allene substrate are described. These include reaction conditions, the nature of the attacking radical, the substitution pattern of the allene, and the length of the linker between the radical center and the proximal allene carbon in the substrate. Cycloaddition reactions between allenes and partners containing π-bonds, which are likely to proceed through radical pathways, are presented to highlight their ability to rapidly access complex polycyclic scaffolds. Finally, the synthetic utility of the products arising from these chemistries is described, including their applications to the construction of complex molecules.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.