Evidence map›Paper›PMID 24758725›Full record

ArticleJournal of the American Chemical Society2014

Palau'chlor: a practical and reactive chlorinating reagent.

Rodrigo A Rodriguez, Chung-Mao Pan, Yuki Yabe, Yu Kawamata, Martin D Eastgate, Phil S Baran

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 48 papers.

0numbers the graph read from it
0cells of the map it votes in
48citing 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

48 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Article
  5. One-Pot Amidation/C─H Halogenation by an Efficient Electrochemical Cascade.Angewandte Chemie (International ed. in English) · 2026
    Article
  6. Nitrosonium Ion-Catalyzed Oxidative Chlorination of Arenes.The Journal of organic chemistry · 2026
    Article
  7. Article
  8. Article
  9. Article
  10. Article
  11. Article
  12. Article
  13. Article
  14. Article
  15. Article
  16. Article
  17. Review
  18. Article
  19. Enantioselective Total Synthesis of (+)-KB343.Journal of the American Chemical Society · 2023
    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

6 authors.

Rodrigo A RodriguezDepartment of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Chung-Mao Pan
Yuki Yabe
Yu Kawamata
Martin D Eastgate
Phil S Baran

Funding

Synthesis of Pyrrole-Imidazole AlkaloidsR01GM073949 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI BARAN, PHIL S · 2005 to 2015
$4.0M
NIGMS NIH HHS GM-073949NIGMS NIH HHS R01 GM073949
6 · The paper itself

Abstract

Unlike its other halogen atom siblings, the utility of chlorinated arenes and (hetero)arenes are twofold: they are useful in tuning electronic structure as well as acting as points for diversification via cross-coupling. Herein we report the invention of a new guanidine-based chlorinating reagent, CBMG or "Palau'chlor", inspired by a key chlorospirocyclization en route to pyrrole imidazole alkaloids. This direct, mild, operationally simple, and safe chlorinating method is compatible with a range of nitrogen-containing heterocycles as well as select classes of arenes, conjugated π-systems, sulfonamides, and silyl enol ethers. Comparisons with other known chlorinating reagents revealed CBMG to be the premier reagent.

Indexed as

AlkaloidsGuanidineHalogenationHydrocarbons, ChlorinatedImidazolesIndicators and ReagentsModels, MolecularPyrrolesAlkaloidsGuanidineHydrocarbons, ChlorinatedimidazoleImidazolesIndicators and ReagentsPyrroles

Identifiers

PMID24758725
PMCPMC4333596

What OpenQuestion holds

Textmetadata
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.