ArticleJournal of the American Chemical Society2022
Rhodium(III)-Catalyzed Anti-Markovnikov Hydroamidation of Unactivated Alkenes Using Dioxazolones as Amidating Reagents.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Transition-Metal Hydride Catalysis Meets Nitrenoid Transfer: Design Principles for Precision C-N Bond Formation.Accounts of chemical research · 2026Article
- Copper-Catalyzed Alkylative Deoxygenation ofMolecules (Basel, Switzerland) · 2026Article
- Enantioselective construction of silicon-stereogenic vinylsilanes from simple alkenes.Nature communications · 2025Article
- Cobalt-Catalyzed (3 + 2) Cycloaddition of Cyclopropene-Tethered Alkynes: Versatile Access to Bicyclic Cyclopentadienyl Systems and Their CpM Complexes.ACS catalysis · 2024Article
- Synthesis of Secondary Amines via Self-Limiting Alkylation.Organic letters · 2024Article
- Rhodium(III)-Catalyzed Remote Hydroamidation of Internal Alkenes via Chain Walking.ACS catalysis · 2023Article
- Progression of Hydroamination Catalyzed by Late Transition-Metal Complexes from Activated to Unactivated Alkenes.Accounts of chemical research · 2023Article
- Copper-catalyzed [1,3]-nitrogen rearrangement ofChemical science · 2023Article
- Remote Hydroamination of Disubstituted Alkenes by a Combination of Isomerization and Regioselective N-H Addition.Journal of the American Chemical Society · 2023Article
Corrections and comments
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Authors and funding
2 authors.
Funding
Abstract
The amide is one of the most prevalent functional groups in all of pharmaceuticals, and for this reason, reactions that introduce the amide moiety are of particular value. Intermolecular hydroamidation of alkenes remains an underexplored method for the synthesis of amide-containing compounds. The majority of hydroamidation procedures exhibit Markovnikov regioselectivity, while current methods for anti-Markovnikov hydroamidation are somewhat limited to activated alkene substrates or radical processes. Herein, we report a general method for the intermolecular anti-Markovnikov hydroamidation of unactivated alkenes under mild conditions, utilizing Rh(III) catalysis in conjunction with dioxazolone amidating reagents and isopropanol as an environmentally friendly hydride source. The reaction tolerates a wide range of functional groups and efficiently converts electron-deficient alkenes, styrenes, and 1,1-disubstituted alkenes, in addition to unactivated alkenes, to their corresponding linear amides. Mechanistic studies reveal a reversible rhodium hydride migratory insertion step, leading to exquisite selectivity for the anti-Markovnikov product.
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Registered trials
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