ArticleNature2013
Alkane desaturation by concerted double hydrogen atom transfer to benzyne.
Article in Nature, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 36 papers.
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Who cites it
36 citing papers in PubMed.
- Phosphorane-Promoted C-C Coupling during Aryne Annulations.Angewandte Chemie (International ed. in English) · 2024Article
- The application of aromaticity and antiaromaticity to reaction mechanisms.Fundamental research · 2023Review
- Advances in the synthesis of nitrogen-containing heterocyclic compounds byRSC advances · 2023Review
- Photocatalytic Abstraction of Hydrogen Atoms from Water Using Hydroxylated Graphitic Carbon Nitride for Hydrogenative Coupling Reactions.Angewandte Chemie (International ed. in English) · 2022Article
- Article
- Radial hexadehydro-Diels-Alder reactions.Chem · 2021Article
- Hexadehydro-Diels-Alder Reaction: Benzyne Generation via Cycloisomerization of Tethered Triynes.Chemical reviews · 2021Review
- Highly Conjugated π-Systems Arising from Cannibalistic Hexadehydro-Diels-Alder Couplings: Cleavage of C-C Single and Triple Bonds.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Direct observation ofChemical science · 2020Article
- Crystal structure of dimethyl 5-(4-ethyl-phen-yl)-4-[(4-ethyl-phen-yl)ethyn-yl]-6,11-diphenyl-1,3,6,11-tetra-hydro-2Acta crystallographica. Section E, Crystallographic communications · 2020Article
- The Aza-hexadehydro-Diels-Alder Reaction.Journal of the American Chemical Society · 2019Article
- Reactions of thermally generated benzynes with six-memberedChemical science · 2019Article
- Consecutive HDDA and TDDA reactions of silicon-tethered tetraynes for the synthesis of dibenzosilole-fused polycyclic compounds and their unique reactivity.Chemical science · 2019Article
- Divergent Reactivity during the Trapping of Benzynes by Glycidol Analogs: Ring Cleavage via Pinacol-Like Rearrangements vs Oxirane Fragmentations.Organic letters · 2019Article
- CuAngewandte Chemie (International ed. in English) · 2018Article
- New Hindered Amide Base for Aryne Insertion into Si-P, Si-S, Si-N, and C-C Bonds.Journal of the American Chemical Society · 2018Article
- The domino hexadehydro-Diels-Alder reaction transforms polyynes to benzynes to naphthynes to anthracynes to tetracynes (and beyond?).Nature chemistry · 2018Article
- Intramolecular hydride transfer onto arynes: redox-neutral and transition metal-free C(spChemical science · 2018Article
- Article
- Aryne cycloaddition reactions of benzodioxasilines as aryne precursors generated by catalytic reductiveTetrahedron · 2017Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
The removal of two vicinal hydrogen atoms from an alkane to produce an alkene is a challenge for synthetic chemists. In nature, desaturases and acetylenases are adept at achieving this essential oxidative functionalization reaction, for example during the biosynthesis of unsaturated fatty acids, eicosanoids, gibberellins and carotenoids. Alkane-to-alkene conversion almost always involves one or more chemical intermediates in a multistep reaction pathway; these may be either isolable species (such as alcohols or alkyl halides) or reactive intermediates (such as carbocations, alkyl radicals, or σ-alkyl-metal species). Here we report a desaturation reaction of simple, unactivated alkanes that is mechanistically unique. We show that benzynes are capable of the concerted removal of two vicinal hydrogen atoms from a hydrocarbon. The discovery of this exothermic, net redox process was enabled by the simple thermal generation of reactive benzyne intermediates through the hexadehydro-Diels-Alder cycloisomerization reaction of triyne substrates. We are not aware of any single-step, bimolecular reaction in which two hydrogen atoms are simultaneously transferred from a saturated alkane. Computational studies indicate a preferred geometry with eclipsed vicinal C-H bonds in the alkane donor.
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Registered trials
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