Evidence map›Paper›PMID 36548788›Full record

ArticleJournal of the American Chemical Society2023

Direct Deaminative Functionalization.

Balu D Dherange, Mingbin Yuan, Christopher B Kelly, Christopher A Reiher, Cristina Grosanu, Kathleen J Berger, Osvaldo Gutierrez, Mark D Levin

Open access · greenAbstract read
In one paragraph

Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 30 papers.

0numbers the graph read from it
0cells of the map it votes in
30citing papers in PubMed
7.6field-weighted citation impact, top 2% 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

30 citing papers in PubMed, 101 citations in OpenAlex.

  1. Direct Deaminative Alkynylation of Aliphatic Primary Amines.Angewandte Chemie (International ed. in English) · 2026
    Article
  2. Article
  3. Review
  4. Innovation (Cambridge (Mass.)) · 2026
    Review
  5. Article
  6. Article
  7. Anomeric Amides: Valuable Reagents in Synthetic Organic Chemistry.Angewandte Chemie (International ed. in English) · 2026
    Review
  8. Article
  9. Article
  10. Article
  11. Article
  12. Article
  13. Deaminative Giese-type reaction.Nature chemistry · 2025
    Article
  14. Photocatalyzed C(spOrganic letters · 2025
    Article
  15. Accessing sulfonamides via formal SONature chemistry · 2025
    Article
  16. Article
  17. Article
  18. Aliphatic Amines Unlocked for Selective Transformations through Diazotization.Angewandte Chemie (International ed. in English) · 2025
    Article
  19. Article
  20. 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

8 authors at 5 institutions in 1 country.

Balu D DherangeDepartment of Chemistry, University of Chicago, Chicago, Illinois 60637, United States.ORCID 0000-0002-4123-5012
Mingbin YuanDepartment of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, United States.
Christopher B KellyDiscovery Process Research, Janssen Research & Development LLC, 1400 McKean Road, Spring House, Pennsylvania 19477, United States.ORCID 0000-0002-5530-8606
Christopher A ReiherParallel Medicinal Chemistry, Janssen Research & Development LLC, 1400 McKean Road, Spring House, Pennsylvania 19477, United States.
Cristina GrosanuHigh Throughput Purification, Janssen Research & Development LLC, 1400 McKean Road, Spring House, Pennsylvania 19477, United States.
Kathleen J BergerDepartment of Chemistry, University of Chicago, Chicago, Illinois 60637, United States.ORCID 0000-0002-7959-6331
Osvaldo GutierrezDepartment of Chemistry, Texas A&M University, College Station, Texas 77843, United States.ORCID 0000-0001-8151-7519
Mark D LevinDepartment of Chemistry, University of Chicago, Chicago, Illinois 60637, United States.ORCID 0000-0002-4461-363X
University of Chicago · USSpringhouse · USJanssen (United States) · USTexas A&M University · USUniversity of Maryland, College Park · US

Funding

New Directions in Sustainable Open-Shell Radical C-C Bond Formations Enabled by Merging Modern Computational and Experimental MethodsR35GM137797 · NIGMS · UNIV OF MARYLAND, COLLEGE PARK · PI Osvaldo Gutierrez · 2020 to 2026
$2.7M
NIGMS NIH HHS R35 GM137797
6 · The paper itself

Abstract

Selective functional group interconversions in complex molecular settings underpin many of the challenges facing modern organic synthesis. Currently, a privileged subset of functional groups dominates this landscape, while others, despite their abundance, are sorely underdeveloped. Amines epitomize this dichotomy; they are abundant but otherwise intransigent toward direct interconversion. Here, we report an approach that enables the direct conversion of amines to bromides, chlorides, iodides, phosphates, thioethers, and alcohols, the heart of which is a deaminative carbon-centered radical formation process using an anomeric amide reagent. Experimental and computational mechanistic studies demonstrate that successful deaminative functionalization relies not only on outcompeting the H-atom transfer to the incipient radical but also on the generation of polarity-matched, productive chain-carrying radicals that continue to react efficiently. The overall implications of this technology for interconverting amine libraries were evaluated via high-throughput parallel synthesis and applied in the development of one-pot diversification protocols.

Indexed as

AmidesAminesBromidesCatalysisChloridesAmidesAminesBromidesChlorides

Identifiers

PMID36548788
PMCPMC10245626
OpenAlexW4312113557

What OpenQuestion holds

Textmetadata
LicenceTDM
Read underepoch 390

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.