Evidence map›Paper›PMID 38769366›Full record

ArticleNature chemistry2024

Discovery of N-X anomeric amides as electrophilic halogenation reagents.

Yu Wang, Cheng Bi, Yu Kawamata, Lauren N Grant, Lacey Samp, Paul F Richardson, Shasha Zhang, Kaid C Harper, Maximilian D Palkowitz, Aristidis Vasilopoulos and 8 more

Abstract read
In one paragraph

Article in Nature chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.

0numbers the graph read from it
0cells of the map it votes in
10citing 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

10 citing papers in PubMed.

  1. Review
  2. Article
  3. Anomeric Amides: Valuable Reagents in Synthetic Organic Chemistry.Angewandte Chemie (International ed. in English) · 2026
    Review
  4. Article
  5. Article
  6. Article
  7. Review
  8. Article
  9. Article
  10. 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

18 authors.

Yu WangDepartment of Chemistry, Scripps Research, La Jolla, CA, USA.
Cheng BiDepartment of Chemistry, Scripps Research, La Jolla, CA, USA.ORCID http://orcid.org/0000-0002-9332-9918
Yu KawamataDepartment of Chemistry, Scripps Research, La Jolla, CA, USA.ORCID http://orcid.org/0000-0002-5515-9612
Lauren N GrantChemical Process Development, Bristol Myers Squibb, New Brunswick, NJ, USA.
Lacey SampChemical Research and Development, Pfizer Inc., Groton, CT, USA.
Paul F RichardsonOncology Medicinal Chemistry Department, Pfizer Medicine Design, San Diego, CA, USA.
Shasha ZhangChemical Process Development, Bristol Myers Squibb, New Brunswick, NJ, USA.
Kaid C HarperAbbVie Process Research and Development, North Chicago, IL, USA.ORCID http://orcid.org/0000-0003-3894-4851
Maximilian D PalkowitzSmall Molecule Drug Discovery, Bristol Myers Squibb, Cambridge, MA, USA.
Aristidis VasilopoulosAdvanced Chemistry Technologies Group, AbbVie Inc., North Chicago, IL, USA.ORCID http://orcid.org/0000-0001-7494-7801
Michael R CollinsOncology Medicinal Chemistry Department, Pfizer Medicine Design, San Diego, CA, USA.ORCID http://orcid.org/0000-0001-7799-1664
Martins S OderindeSmall Molecule Discovery Chemistry, Bristol Myers Squibb Research and Early Development, Princeton, NJ, USA.
Chet C TyrolPfizer Medicine Design, Groton, CT, USA.
Doris ChenOncology Medicinal Chemistry Department, Pfizer Medicine Design, San Diego, CA, USA.
Erik A LaChapellePfizer Medicine Design, Groton, CT, USA.
Jake B BaileyDepartment of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA, USA.ORCID http://orcid.org/0000-0002-4659-8189
Jennifer X QiaoSmall Molecule Drug Discovery, Bristol Myers Squibb, Cambridge, MA, USA.ORCID http://orcid.org/0000-0002-6685-2092
Phil S BaranDepartment of Chemistry, Scripps Research, La Jolla, CA, USA. pbaran@scripps.edu.ORCID http://orcid.org/0000-0001-9193-9053

Funding

Scalable Synthesis and New Bond DisconnectionsR35GM118176 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI BARAN, PHIL S · 2016 to 2025
$11.5M
NIGMS NIH HHS R35 GM118176U.S. Department of Health & Human Services | National Institutes of Health (NIH) GM-118176
6 · The paper itself

Abstract

Electrophilic halogenation is a widely used tool employed by medicinal chemists to either pre-functionalize molecules for further diversity or incorporate a halogen atom into drugs or drug-like compounds to solve metabolic problems or modulate off-target effects. Current methods to increase the power of halogenation rely on either the invention of new reagents or activating commercially available reagents with various additives such as Lewis or Brønsted acids, Lewis bases and hydrogen-bonding activators. There is a high demand for new reagents that can halogenate otherwise unreactive compounds under mild conditions. Here we report the invention of a class of halogenating reagents based on anomeric amides, taking advantage of the energy stored in the pyramidalized nitrogen of N-X anomeric amides as a driving force. These robust halogenating methods are compatible with a variety of functional groups and heterocycles, as exemplified on over 50 compounds (including 13 gram-scale examples and 1 flow chemistry scale-up).

Identifiers

PMID38769366
PMCPMC11457727

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Registered trials

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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.