ArticleJournal of the American Chemical Society2014
C-H methylation of heteroarenes inspired by radical SAM methyl transferase.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 35 papers.
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Who cites it
35 citing papers in PubMed.
- Harnessing the Reactivity of Sulfinate Salts With Cystine: An Umpolung Approach to Residue-Specific Peptide Modification.Angewandte Chemie (International ed. in English) · 2026Article
- Bioinspired transfer methylation enabled by a photoactive reagent.Nature communications · 2025Article
- Meta-Dimethylation of Arenes via Catellani Reaction from Aryl Thianthrenium Salts.Angewandte Chemie (International ed. in English) · 2025Article
- Crafting mono- and novel bis-methylated pyrroloquinoxaline derivatives from a shared precursor and its application in the total synthesis of marinoquinoline A.RSC advances · 2023Article
- Sulfonium-based precise alkyl transposition reactions.Science advances · 2023Article
- Fluorescent labeling of RNA and DNA on the Hoogsteen edge using sulfinate chemistry.RNA (New York, N.Y.) · 2023Article
- Regiodivergent synthesis of sulfone-tethered lactam-lactones bearing four contiguous stereocenters.RSC advances · 2023Article
- Photoinduced Cascade Reactions of 2-Allylphenol Derivatives toward the Production of 2,3-Dihydrobenzofurans.The Journal of organic chemistry · 2023Article
- Ruthenium-Catalyzed Monoselective C-H Methylation andJACS Au · 2022Article
- Structure and Catalytic Mechanism of Radical SAM Methylases.Life (Basel, Switzerland) · 2022Review
- Ni-catalyzed hydroarylation of alkynes with unactivated β-C(spNature communications · 2022Article
- Reductant-Free Cross-Electrophile Synthesis of Di(hetero)arylmethanes by Palladium-Catalyzed Desulfinative C-C Coupling.Angewandte Chemie (International ed. in English) · 2022Article
- The Photochemical Activity of a Halogen-Bonded Complex Enables the Microfluidic Light-Driven Alkylation of Phenols.Organic letters · 2022Article
- Direct Deamination of Primary Amines via Isodiazene Intermediates.Journal of the American Chemical Society · 2021Article
- Recent Advances in Photoredox-Mediated Radical Conjugate Addition Reactions: An Expanding Toolkit for the Giese Reaction.Angewandte Chemie (International ed. in English) · 2021Review
- The Deuterated "Magic Methyl" Group: A Guide to Site-Selective Trideuteromethyl Incorporation and Labeling by Using CDChemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- Iridium-catalyzed C-H methylation andiScience · 2021Article
- A Titanium-Catalyzed Reductive α-Desulfonylation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Synthesis of quaternary centres by single electron reduction and alkylation of alkylsulfones.Chemical science · 2021Article
- Bioinspired design of a robustScience advances · 2020Article
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Authors and funding
9 authors.
Funding
Abstract
A practical C-H functionalization method for the methylation of heteroarenes is presented. Inspiration from Nature's methylating agent, S-adenosylmethionine (SAM), allowed for the design and development of zinc bis(phenylsulfonylmethanesulfinate), or PSMS. The action of PSMS on a heteroarene generates a (phenylsulfonyl)methylated intermediate that can be easily separated from unreacted starting material. This intermediate can then be desulfonylated to the methylated product or elaborated to a deuteriomethylated product, and can divergently access medicinally important motifs. This mild, operationally simple protocol that can be conducted in open air at room temperature is compatible with sensitive functional groups for the late-stage functionalization of pharmacologically relevant substrates.
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