Evidence map›Paper›PMID 32975859›Full record

ArticleAngewandte Chemie (International ed. in English)2021

Diversification of Unprotected Alicyclic Amines by C-H Bond Functionalization: Decarboxylative Alkylation of Transient Imines.

Anirudra Paul, Jae Hyun Kim, Scott D Daniel, Daniel Seidel

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.

0numbers the graph read from it
0cells of the map it votes in
17citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

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

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

17 citing papers in PubMed.

  1. Deciphering competing reaction pathways in the α-C-H functionalization of unprotected alicyclic aminesOrganic chemistry frontiers : an international journal of organic chemistry · 2026
    Article
  2. Article
  3. Review
  4. Cyclic Imine-BFSynlett : accounts and rapid communications in synthetic organic chemistry · 2025
    Article
  5. Photocatalytic Decarboxylative Alkylation of Cyclic Imine-BFJournal of the American Chemical Society · 2024
    Article
  6. Article
  7. Article
  8. Alicyclic-Amine-Derived Imine-BFAngewandte Chemie (International ed. in English) · 2024
    Article
  9. Article
  10. Article
  11. Article
  12. Review
  13. Article
  14. Article
  15. Article
  16. Article
  17. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

4 authors.

Anirudra PaulCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL, 32611, USA.
Jae Hyun KimCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL, 32611, USA.
Scott D DanielCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL, 32611, USA.
Daniel SeidelCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL, 32611, USA.ORCID 0000-0001-6725-111X

Funding

Development of Strategies for the Functionalization of AminesR01GM101389 · NIGMS · UNIVERSITY OF FLORIDA · PI SEIDEL, DANIEL · 2012 to 2021
$2.5M
Acquisition of a Q Exactive HF Hybrid Quadrupole-OrbitrapS10OD021758 · OD · UNIVERSITY OF FLORIDA · PI BASSO, KARI B · 2017 to 2017
$600k
NIGMS NIH HHS R01 GM101389NIGMS NIH HHS R01GM101389NIH HHS S10 OD021758
6 · The paper itself

Abstract

Despite extensive efforts by many practitioners in the field, methods for the direct α-C-H bond functionalization of unprotected alicyclic amines remain rare. A new advance in this area utilizes N-lithiated alicyclic amines. These readily accessible intermediates are converted to transient imines through the action of a simple ketone oxidant, followed by alkylation with a β-ketoacid under mild conditions to provide valuable β-amino ketones with unprecedented ease. Regioselective α'-alkylation is achieved for substrates with existing α-substituents. The method is further applicable to the convenient one-pot synthesis of polycyclic dihydroquinolones through the incorporation of a S

Indexed as

AlkylationAminesCarbonHydrogenIminesMolecular StructureAminesCarbonHydrogenIminesalicyclic aminesannulationC−C bond formationC−H bond functionalizationMannich reaction

Identifiers

PMID32975859
PMCPMC7854982

What OpenQuestion holds

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Registered trials

None linked

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.