Evidence map›Paper›PMID 36036764›Full record

ArticleOrganic letters2022

Regioselective α-Cyanation of Unprotected Alicyclic Amines.

Fuchao Yu, Daniel A Valles, Weijie Chen, Scott D Daniel, Ion Ghiviriga, Daniel Seidel

Open access · greenAbstract read
In one paragraph

Article in Organic letters, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.

0numbers the graph read from it
0cells of the map it votes in
8citing papers in PubMed
1.9field-weighted citation impact, top 15% of its field
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

8 citing papers in PubMed, 17 citations in OpenAlex.

  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. Cyclic Imine-BFSynlett : accounts and rapid communications in synthetic organic chemistry · 2025
    Article
  3. Photocatalytic Decarboxylative Alkylation of Cyclic Imine-BFJournal of the American Chemical Society · 2024
    Article
  4. Article
  5. Alicyclic-Amine-Derived Imine-BFAngewandte Chemie (International ed. in English) · 2024
    Article
  6. Article
  7. Article
  8. 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

6 authors at 2 institutions in 2 countries.

Fuchao YuCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.ORCID 0000-0001-5557-3824
Daniel A VallesCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.
Weijie ChenCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.ORCID 0000-0002-9501-4848
Scott D DanielCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.
Ion GhivirigaCenter for NMR Spectroscopy, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.ORCID 0000-0001-5812-5170
Daniel SeidelCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.ORCID 0000-0001-6725-111X
University of Florida · USKunming University of Science and Technology · CN

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 GM101389NIH HHS S10 OD021758
6 · The paper itself

Abstract

Secondary alicyclic amines are converted to α-aminonitriles via addition of TMSCN to their corresponding imines, intermediates that are produced in situ via the oxidation of amine-derived lithium amides with simple ketone oxidants. Amines with an existing α-substituent undergo regioselective α'-cyanation even if the C-H bonds at that site are less activated. Amine α-arylation can be combined with α'-cyanation to generate difunctionalized products in a single operation.

Identifiers

PMID36036764
PMCPMC9548390
OpenAlexW4293462345

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.