Evidence map›Paper›PMID 37321182›Full record

ArticleThe Journal of organic chemistry2023

Ni-Catalyzed Enantioselective Intramolecular Mizoroki-Heck Reaction for the Synthesis of Phenanthridinone Derivatives.

Diana Rachii, Dana J Caldwell, Yui Kosukegawa, Mary Sexton, Paul R Rablen, William P Malachowski

Abstract read
In one paragraph

Article in The Journal of organic chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing 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

2 citing papers in PubMed.

  1. Review
  2. Formal Synthesis ofMolecules (Basel, Switzerland) · 2026
    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.

Diana RachiiChemistry Department, Bryn Mawr College, Bryn Mawr, Pennsylvania 19010, United States.
Dana J CaldwellChemistry Department, Bryn Mawr College, Bryn Mawr, Pennsylvania 19010, United States.ORCID 0000-0002-7205-4222
Yui KosukegawaChemistry Department, Bryn Mawr College, Bryn Mawr, Pennsylvania 19010, United States.
Mary SextonChemistry Department, Bryn Mawr College, Bryn Mawr, Pennsylvania 19010, United States.
Paul R RablenChemistry Department, Swarthmore College, Swarthmore, Pennsylvania 19081, United States.ORCID 0000-0002-1300-1999
William P MalachowskiChemistry Department, Bryn Mawr College, Bryn Mawr, Pennsylvania 19010, United States.ORCID 0000-0003-1215-3808

Funding

The enantioselective synthesis of new phenanthridinone and carbazole analogs with quaternary and tertiary carbons using the Birch-Heck sequenceR15GM123475 · NIGMS · BRYN MAWR COLLEGE · PI MALACHOWSKI, WILLIAM P · 2018 to 2018
$363k
NIGMS NIH HHS R15 GM123475
6 · The paper itself

Abstract

A Ni-catalyzed enantioselective intramolecular Mizoroki-Heck reaction has been developed to transform symmetrical 1,4-cyclohexadienes with attached aryl halides into phenanthridinone analogues containing quaternary stereocenters. Herein, we report important advances in reaction optimization enabling control of unwanted proto-dehalogenation and alkene reduction side products. Moreover, this approach provides direct access to six-membered ring heterocyclic systems bearing all-carbon quaternary stereocenters, which have been much more challenging to form enantioselectively with nickel-catalyzed Heck reactions. A wide range of substrates were demonstrated to work in good to excellent yields. Good enantioselectivity was demonstrated using a new synthesized chiral

Indexed as

NickelPalladiumCatalysisMolecular StructureStereoisomerismNickelPalladium

Identifiers

PMID37321182
PMCPMC10337041

What OpenQuestion holds

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LicenceCC BY
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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.