Evidence map›Paper›PMID 27404018›Full record

ArticleOrganic letters2016

Synthesis of Indole-2-carboxylate Derivatives via Palladium-Catalyzed Aerobic Amination of Aryl C-H Bonds.

Kyle Clagg, Haiyun Hou, Adam B Weinstein, David Russell, Shannon S Stahl, Stefan G Koenig

Abstract read
In one paragraph

Article in Organic letters, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.

0numbers the graph read from it
0cells of the map it votes in
4citing 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

4 citing papers in PubMed.

  1. Article
  2. Synthesis of indoles, indolines, and carbazolesGreen synthesis and catalysis · 2021
    Article
  3. Article
  4. 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.

Kyle ClaggSmall Molecule Process Chemistry, Genentech, Inc. , 1 DNA Way, South San Francisco, California 94080, United States.
Haiyun HouSmall Molecule Process Chemistry, Genentech, Inc. , 1 DNA Way, South San Francisco, California 94080, United States.
Adam B WeinsteinDepartment of Chemistry, University of Wisconsin-Madison , 1101 University Avenue, Madison, Wisconsin 53706, United States.
David RussellSmall Molecule Analytical Chemistry and Quality Control, Genentech, Inc. , 1 DNA Way, South San Francisco, California 94080, United States.
Shannon S StahlDepartment of Chemistry, University of Wisconsin-Madison , 1101 University Avenue, Madison, Wisconsin 53706, United States.
Stefan G KoenigSmall Molecule Process Chemistry, Genentech, Inc. , 1 DNA Way, South San Francisco, California 94080, United States.

Funding

Palladium-Catalyzed Oxidative Amination of AlkenesR01GM067173 · NIGMS · UNIVERSITY OF WISCONSIN-MADISON · PI STAHL, SHANNON S · 2003 to 2015
$3.6M
NIGMS NIH HHS R01 GM067173
6 · The paper itself

Abstract

A direct oxidative C-H amination affording 1-acetyl indolecarboxylates starting from 2-acetamido-3-arylacrylates has been achieved. Indole-2-carboxylates can be targeted with a straightforward deacetylation of the initial reaction products. The C-H amination reaction is carried out using a catalytic Pd(II) source with oxygen as the terminal oxidant. The scope and application of this chemistry is demonstrated with good to high yields for numerous electron-rich and electron-poor substrates. Further reaction of selected products via Suzuki arylation and deacetylation provides access to highly functionalized indole structures.

Indexed as

AminationCatalysisIndolesMolecular StructureOrganometallic CompoundsPalladiumindole-2-carboxylateIndolesOrganometallic CompoundsPalladium

Identifiers

PMID27404018
PMCPMC5296645

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.