Evidence map›Paper›PMID 29498847›Full record

ArticleThe Journal of organic chemistry2018

Copper-Catalyzed Chan-Lam Cyclopropylation of Phenols and Azaheterocycles.

Joseph Derosa, Miriam L O'Duill, Matthew Holcomb, Mark N Boulous, Ryan L Patman, Fen Wang, Michelle Tran-Dubé, Indrawan McAlpine, Keary M Engle

Abstract read
In one paragraph

Article in The Journal of organic chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.

0numbers the graph read from it
0cells of the map it votes in
5citing 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

5 citing papers in PubMed.

  1. Article
  2. Article
  3. A GeneralChem · 2021
    Article
  4. Article
  5. 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

9 authors.

Joseph DerosaDepartment of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.
Miriam L O'DuillDepartment of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.
Matthew HolcombDepartment of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.
Mark N BoulousDepartment of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.
Ryan L PatmanPfizer Oncology Medicinal Chemistry , 10770 Science Center Drive , San Diego , California 92121 , United States.
Fen WangPfizer Oncology Medicinal Chemistry , 10770 Science Center Drive , San Diego , California 92121 , United States.
Michelle Tran-DubéPfizer Oncology Medicinal Chemistry , 10770 Science Center Drive , San Diego , California 92121 , United States.
Indrawan McAlpinePfizer Oncology Medicinal Chemistry , 10770 Science Center Drive , San Diego , California 92121 , United States.
Keary M EngleDepartment of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.ORCID 0000-0003-2767-6556

Funding

Combinatorial, Catalytic Functionalization of Alkenes and AlkynesR35GM125052 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI ENGLE, KEARY MARK · 2017 to 2021
$2.9M
NIGMS NIH HHS R35 GM125052
6 · The paper itself

Abstract

Small molecules containing cyclopropane-heteroatom linkages are commonly needed in medicinal chemistry campaigns yet are problematic to prepare using existing methods. To address this issue, a scalable Chan-Lam cyclopropylation reaction using potassium cyclopropyl trifluoroborate has been developed. With phenol nucleophiles, the reaction effects O-cyclopropylation, whereas with 2-pyridones, 2-hydroxybenzimidazoles, and 2-aminopyridines the reaction brings about N-cyclopropylation. The transformation is catalyzed by Cu(OAc)

Indexed as

Aza CompoundsCatalysisCopperCyclopropanesHeterocyclic CompoundsMolecular StructurePhenolsAza CompoundsCopperCyclopropanesHeterocyclic CompoundsPhenols

Identifiers

PMID29498847
PMCPMC6003411

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.