Evidence map›Paper›PMID 35076246›Full record

ArticleThe Journal of organic chemistry2022

Directed Palladium-Catalyzed Acetoxylation of Indolines. Total Synthesis of

Kristen M Flynn, Kolby L White, Mohammad Movassaghi

Open access · greenAbstract read
In one paragraph

Article in The Journal of organic chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it
0cells of the map it votes in
1citing papers in PubMed
1.1field-weighted citation impact, top 26% 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

1 citing paper in PubMed, 6 citations in OpenAlex.

  1. 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

3 authors at 1 institution in 1 country.

Kristen M FlynnDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
Kolby L WhiteDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
Mohammad MovassaghiDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.ORCID 0000-0003-3080-1063
Massachusetts Institute of Technology · US

Funding

Synthesis and Study of Complex Natural ProductsR01GM074825 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI MOVASSAGHI, MOHAMMAD · 2005 to 2019
$4.6M
Development of New Strategies for Chemical Synthesis and Study of Complex Natural ProductsR35GM141963 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI Mohammad Movassaghi · 2021 to 2026
$4.3M
NIGMS NIH HHS R01 GM074825NIGMS NIH HHS R35 GM141963
6 · The paper itself

Abstract

We describe a palladium-catalyzed C7-acetoxylation of indolines with a range of amide directing groups. While a variety of substituents are tolerated on the indoline-core and the N1-acyl group, the acetoxylation is most sensitive to the C2- and C6-indoline substituents. The practicality of this indoline C7-acetoxylation is demonstrated using a cinnamamide substrate on a mmol scale. Several N1-acyl groups, including those present in natural alkaloids, guide C7-acetoxylation of indoline substrates over a competitive C5-oxidation. The application of this chemistry allowed for the first synthesis of

Indexed as

AlkaloidsPalladiumCatalysisIndolesAlkaloidsIndolesindolinePalladium

Identifiers

PMID35076246
PMCPMC9020104
OpenAlexW4220745497

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.