Evidence map›Paper›PMID 20858012›Full record

ArticleJournal of the American Chemical Society2010

Synthesis of heterocycles via Pd-ligand controlled cyclization of 2-chloro-N-(2-vinyl)aniline: preparation of carbazoles, indoles, dibenzazepines, and acridines.

Dmitry Tsvelikhovsky, Stephen L Buchwald

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.

0numbers the graph read from it
0cells of the map it votes in
16citing 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

16 citing papers in PubMed.

  1. Review
  2. Article
  3. Iodine(III)-Mediated Oxidation of Anilines to Construct Dibenzazepines.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023
    Article
  4. Strategies in the synthesis of dibenzo[Beilstein journal of organic chemistry · 2023
    Review
  5. Article
  6. Interrupted Intramolecular Hydroaminomethylation ofMolecules (Basel, Switzerland) · 2022
    Article
  7. Article
  8. Article
  9. Article
  10. Article
  11. Article
  12. Article
  13. Copper-catalyzed oxidative amination and allylic amination of alkenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2013
    Article
  14. Article
  15. Article
  16. Copper-Catalyzed Synthesis ofSynlett : accounts and rapid communications in synthetic organic chemistry
    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

2 authors.

Dmitry TsvelikhovskyDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Stephen L Buchwald

Funding

LATE TRANSITION METAL CATALYSTS FOR ORGANIC SYNTHESISR01GM058160 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI BUCHWALD, STEPHEN L · 1998 to 2016
$9.0M
CATALYTIC METHODS FOR ORGANIC SYNTHESISR37GM046059 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI BUCHWALD, STEPHEN L · 2000 to 2009
$8.1M
NIGMS NIH HHS GM-58160NIGMS NIH HHS R01 GM058160NIGMS NIH HHS R37 GM046059
6 · The paper itself

Abstract

The Pd-catalyzed condensation of 2-bromostyrene and 2-chloroaniline derivatives yields stable diphenylamine intermediates, which are selectively converted to five-, six-, or seven-membered heteroaromatics (indoles, carbazoles, acridines, and dibenzazepines). The selectivity of these intramolecular transformations is uniquely ligand-controlled and offers efficient routes to four important classes of heterocycles from a common precursor.

Indexed as

AcridinesAniline CompoundsCarbazolesCyclizationDibenzazepinesHeterocyclic CompoundsIndolesLigandsPalladium2-chloroanilineAcridinesAniline CompoundsCarbazolesDibenzazepinesHeterocyclic CompoundsIndolesLigandsPalladium

Identifiers

PMID20858012
PMCPMC2951481

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.