Remote Desaturation of Unprotected Amines and C─H Amination of Alkanes by Polarity-Matched N-Radical Cations.

Pavitra Laohapaisan, Ross M Dare, Meredith L Rudich, Jacob J A Garwood, Siyuan Gong, R Thomas Simons, David A Nagib

Abstract read

In one paragraph

Article in Angewandte Chemie (International ed. in English), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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1 · What the graph read from it

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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

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3 · Its place in the literature

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0 citing papers in PubMed.

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4 · The record

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5 · Who and what money

Authors and funding

7 authors.

Pavitra LaohapaisanDepartment of Chemistry and Biochemistry, The Ohio State University, Columbus, Ohio, USA.ORCID https://orcid.org/0000-0002-1304-813X

Ross M DareDepartment of Chemistry and Biochemistry, The Ohio State University, Columbus, Ohio, USA.ORCID https://orcid.org/0000-0002-1672-8093

Meredith L RudichDepartment of Chemistry and Biochemistry, The Ohio State University, Columbus, Ohio, USA.ORCID https://orcid.org/0009-0002-6818-200X

Jacob J A GarwoodDepartment of Chemistry and Biochemistry, The Ohio State University, Columbus, Ohio, USA.ORCID https://orcid.org/0009-0000-2848-0868

Siyuan GongDepartment of Chemistry and Biochemistry, The Ohio State University, Columbus, Ohio, USA.ORCID https://orcid.org/0009-0009-5979-9041

R Thomas SimonsDepartment of Chemistry and Biochemistry, The Ohio State University, Columbus, Ohio, USA.ORCID https://orcid.org/0000-0002-5799-5737

David A NagibDepartment of Chemistry and Biochemistry, The Ohio State University, Columbus, Ohio, USA.ORCID https://orcid.org/0000-0002-2275-6381

Funding

Radical Chaperones to Harness Remote, Selective C-H Functionalization MechanismsR35GM119812 · NIGMS · OHIO STATE UNIVERSITY · PI NAGIB, DAVID A · 2016 to 2025

$4.0M

Brown Institute for Basic SciencesNIGMS NIH HHS R35 GM119812NIH HHS R35 GM119812Ohio Supercomputer Center

6 · The paper itself

Abstract

A CuCl-catalyzed strategy enables practical, selective, and efficient δ desaturation of unprotected amines. These bifunctional molecules allow rapid conversion of simple amines to privileged heterocycles in medicine. The key radical relay mechanism is an interrupted Hofmann-Löffler-Freytag (HLF) reaction, which may now be carried out without protecting groups. Based on 'radical polarity matching' analysis, we show here that N-radical cations are ideal intermediates for facilitating efficient and selective 1,5-H-atom transfer (HAT) of unprotected amines. Mechanistic probes illustrate the scope, rate, selectivity, and utility of these distal amino alkenes. Computational studies compare the importance of kinetic (radical polarity) over thermodynamic (bond strength) factors in predicting HAT reactivity. Extension to an intermolecular variant allows the direct, desaturative C─H amination of alkanes in a net triple C─H functionalization.

Indexed as

C─H aminationC─H functionalizationheterocyclesN‐radical cationsprotecting‐group free

Identifiers

PMID42555163

DOI10.1002/anie.4933839

PMCPMC13618280

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.