ArticleNature chemistry2015
A manganese catalyst for highly reactive yet chemoselective intramolecular C(sp(3))-H amination.
Article in Nature chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 71 papers.
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71 citing papers in PubMed.
- Remapping the Synthetic Landscape of α-Tertiary Alkylamines via Dual-Functional Catechol.Angewandte Chemie (International ed. in English) · 2026Article
- Silver-catalysed intermolecular benzylic-selective C-H amidationChemical science · 2026Article
- Frontiers in manganese catalysis: a sustainable platform for bond construction and heterocycle synthesis.RSC advances · 2026Review
- Photoinduced Mn catalysis for efficient platform for C-heteroatom bond coupling of aryl halides.Nature communications · 2026Article
- Merging Double Hydrogen Atom Transfer and Stepwise Proton-Coupled Electron Transfer for γ‑C-H Hydrazination of Alcohols.JACS Au · 2026Article
- Comparative Nitrene-Transfer Chemistry to Olefins Mediated by First-Row Transition Metal Catalysts Supported by a Pyridinophane Macrocycle with N4 Ligation.Molecules (Basel, Switzerland) · 2025Article
- Catalytic Metalloradical System for Radical 1,6-C(spJournal of the American Chemical Society · 2025Article
- Identification of a Selective Anticancer Agent from a Collection of Complex-And-Diverse Compounds Synthesized from Stevioside.Journal of the American Chemical Society · 2025Article
- Manganese(I)-Catalyzed Enantioselective Alkylation To Access P-Stereogenic Phosphines.Journal of the American Chemical Society · 2025Article
- Catalytic Asymmetric Cycloaddition of Olefins with In Situ GeneratedJournal of the American Chemical Society · 2024Article
- Exploration of One-Pot, Tandem Sulfamoylation andThe Journal of organic chemistry · 2024Article
- C-H functionalization of camphor through emerging approaches.Chemistry letters · 2024Review
- Taming Tethered Nitreniums for Alkene Functionalization Reactions.The Journal of organic chemistry · 2024Article
- The Development of a Sulfamate-Tethered Aza-Michael Cyclization Allows for the Preparation of (-)-NegamycinThe Journal of organic chemistry · 2024Article
- Sulfamate-Tethered Aza-Wacker Strategy for a Kasugamine Synthon.The Journal of organic chemistry · 2024Article
- Coumarin C-H Functionalization by Mn(I) Carbonyls: Mechanistic Insight by Ultra-Fast IR Spectroscopic Analysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Sulfur(iv) reagents for the SuFEx-based synthesis of substituted sulfamate esters.Chemical science · 2023Article
- Sulfamate-TetheredThe Journal of organic chemistry · 2023Article
- Kukhtin-Ramirez-Reaction-Inspired Deprotection of Sulfamidates for the Synthesis of Amino Sugars.Molecules (Basel, Switzerland) · 2022Article
- Silver Catalyzed Site-Selective C(spMolecules (Basel, Switzerland) · 2022Article
11 more citing papers are in PubMed but not listed here.
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6 authors.
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Abstract
C-H bond oxidation reactions underscore the existing paradigm wherein high reactivity and high selectivity are inversely correlated. The development of catalysts capable of oxidizing strong aliphatic C(sp(3))-H bonds while displaying chemoselectivity (that is, tolerance of more oxidizable functionality) remains an unsolved problem. Here, we describe a catalyst, manganese tert-butylphthalocyanine [Mn((t)BuPc)], that is an outlier to the reactivity-selectivity paradigm. It is unique in its capacity to functionalize all types of C(sp(3))-H bond intramolecularly, while displaying excellent chemoselectivity in the presence of π functionality. Mechanistic studies indicate that [Mn((t)BuPc)] transfers bound nitrenes to C(sp(3))-H bonds via a pathway that lies between concerted C-H insertion, observed with reactive noble metals such as rhodium, and stepwise radical C-H abstraction/rebound, as observed with chemoselective base metals such as iron. Rather than achieving a blending of effects, [Mn((t)BuPc)] aminates even 1° aliphatic and propargylic C-H bonds, demonstrating reactivity and selectivity unusual for previously known catalysts.
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