Evidence map›Paper›PMID 26990693›Full record

ArticleChemistry (Weinheim an der Bergstrasse, Germany)2016

Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates.

Enxuan Zhang, Jiaze Tang, Suhua Li, Peng Wu, John E Moses, K Barry Sharpless

Open access · greenAbstract read
In one paragraph

Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.

0numbers the graph read from it
0cells of the map it votes in
14citing papers in PubMed
8.3field-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

14 citing papers in PubMed, 86 citations in OpenAlex.

  1. Article
  2. Article
  3. Review
  4. Review
  5. Article
  6. Article
  7. Article
  8. Article
  9. Article
  10. Article
  11. Biocompatible SuFEx Click Chemistry: Thionyl Tetrafluoride (SOFAngewandte Chemie (International ed. in English) · 2019
    Article
  12. Installation of -SOBeilstein journal of organic chemistry · 2019
    Article
  13. SuFEx Chemistry of Thionyl Tetrafluoride (SOFAngewandte Chemie (International ed. in English) · 2018
    Article
  14. 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 3 institutions in 3 countries.

Enxuan ZhangAsymchem Life Science (Tianjin) Co., Ltd., 71 7th Avenue, TEDA, Tianjin, 300457, P. R. China. zhangenxuan@asymchem.com.cn.
Jiaze TangAsymchem Life Science (Tianjin) Co., Ltd., 71 7th Avenue, TEDA, Tianjin, 300457, P. R. China.
Suhua LiDepartment of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
Peng WuDepartment of Chemical Physiology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
John E MosesSchool of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK.
K Barry SharplessDepartment of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA. sharples@scripps.edu.
Scripps Research Institute · USTianjin Economic-Technological Development Area · CNUniversity of Nottingham · GB

Funding

Project 9P50GM103368 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI ARNOLD, EDWARD · 2012 to 2016
$20.0M
Sulfur(VI) Fluoride Exchange (SuFEx): new developments and biological applicationsR01GM117145 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI SHARPLESS, KARL BARRY · 2016 to 2023
$3.9M
NIGMS NIH HHS P50 GM103368NIGMS NIH HHS R01 GM117145
6 · The paper itself

Abstract

A selection of heteroaryl fluorosulfates were readily synthesized using commercial SO2F2 gas. These substrates are highly efficient coupling partners in the Suzuki reaction. Through judicious selection of Pd catalysts the fluorosulfate functionality is differentiated from bromide and chloride; the order of reactivity being: -Br> -OSO2 F> -Cl. Exploiting this trend allowed the stepwise chemoselective synthesis of a number of polysubstituted pyridines, including the drug Etoricoxib.

Indexed as

CatalysisEtoricoxibMolecular StructurePalladiumPyridinesSulfonesEtoricoxibPalladiumPyridinesSulfoneschemoselectivitycross-coupling reactionsfluorosulfatespalladiumpolysubstituted pyridineSuzuki reaction

Identifiers

PMID26990693
PMCPMC4929982
OpenAlexW2298033103

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.