ArticleChemical science2020
Iron-catalyzed α-C-H functionalization of π-bonds: cross-dehydrogenative coupling and mechanistic insights.
Article in Chemical science, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- An Organometallic Umpolung Approach for Iron-Mediated Propargylic C-H Etherification.Angewandte Chemie (International ed. in English) · 2024Article
- Iridium-Catalyzed Enantioselective Propargylic C-H Trifluoromethylthiolation and Related Processes.Journal of the American Chemical Society · 2024Article
- Accessing Z-Enynes via Cobalt-Catalyzed Propargylic Dehydrogenation.Angewandte Chemie (International ed. in English) · 2024Article
- A C-H functionalization approach to diverse nitrogenous scaffolds through conjugate addition of catalytic allyliron nucleophiles.Chemical science · 2024Article
- Synthesis of 1,3-Enynes by Iron-Catalyzed Propargylic C-H Functionalization: An Alkyne Analogue for the Eschenmoser Methenylation.Organic letters · 2024Article
- Enantioselective and Regiodivergent Synthesis of Propargyl- and Allenylsilanes through Catalytic Propargylic C-H Deprotonation.Angewandte Chemie (International ed. in English) · 2024Article
- Iron-Mediated C-H Functionalization of Unactivated Alkynes for the Synthesis of Derivatized Dihydropyrrolones: Regioselectivity Under Thermodynamic Control.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Iron-Catalyzed Coupling of Alkenes and Enones: Sakurai-Michael-type Conjugate Addition of Catalytic Allyliron Nucleophiles.Organic letters · 2023Article
- Designed Iron Catalysts for Allylic C-H Functionalization of Propylene and Simple Olefins.Angewandte Chemie (International ed. in English) · 2023Article
- Enantioselective and Diastereodivergent Allylation of Propargylic C-H Bonds.Journal of the American Chemical Society · 2022Article
- Contrasteric coupling of allenes and tetrahydroisoquinolines by iron-catalysed allenic C(spChemical communications (Cambridge, England) · 2021Article
- Iron-Catalyzed Contrasteric Functionalization of Allenic C(spJournal of the American Chemical Society · 2021Article
- C-H Bond Functionalization of Amines: A Graphical Overview of Diverse Methods.SynOpen (2017) · 2021Article
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Authors and funding
5 authors.
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No grant is acknowledged in the PubMed record.
Abstract
The deprotonation of propargylic C-H bonds for subsequent functionalization typically requires stoichiometric metal alkyl or amide reagents. In addition to the undesirable generation of stoichiometric metallic waste, these conditions limit the functional group compatibility and versatility of this functionalization strategy and often result in regioisomeric mixtures. In this article, we report the use of dicarbonyl cyclopentadienyliron(ii) complexes for the generation of propargylic anion equivalents toward the direct electrophilic functionalization of propargylic C-H bonds under mild, catalytic conditions. This technology was applied to the direct conversion of C-H bonds to C-C bonds for the synthesis of several functionalized scaffolds through a one-pot cross dehydrogenative coupling reaction with tetrahydroisoquinoline and related privileged heterocyclic scaffolds. A series of NMR studies and deuterium-labelling experiments indicated that the deprotonation of the propargylic C-H bond was the rate-determining step when a Cp*Fe(CO)
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