Evidence map›Paper›PMID 36307409›Full record

ArticleNature communications2022

Dearomatization of aromatic asmic isocyanides to complex cyclohexadienes.

Bilal Altundas, Embarek Alwedi, Zhihui Song, Achyut Ranjan Gogoi, Ryan Dykstra, Osvaldo Gutierrez, Fraser F Fleming

Abstract read
In one paragraph

Article in Nature communications, 2022. 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. Article
  2. Interrupted SJACS Au · 2024
    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

7 authors.

Bilal AltundasDepartment of Chemistry, Drexel University, 3401 Chestnut St., Philadelphia, PA, 19104, USA.
Embarek AlwediMerck Inc., 90 E. Scott Ave, Rahway, NJ, 07065, USA.ORCID 0000-0002-7031-2427
Zhihui SongDepartment of Chemistry and Biochemistry, University of Maryland, 8051 Reagents Drive, College Park, MD, 20742, USA.
Achyut Ranjan GogoiDepartment of Chemistry, Texas A&M University, Ross @ Spence St, College Station, TX, 77843, USA.ORCID 0000-0002-7609-3720
Ryan DykstraDepartment of Chemistry and Biochemistry, University of Maryland, 8051 Reagents Drive, College Park, MD, 20742, USA.
Osvaldo GutierrezDepartment of Chemistry, Texas A&M University, Ross @ Spence St, College Station, TX, 77843, USA. og.labs@tamu.edu.
Fraser F FlemingDepartment of Chemistry, Drexel University, 3401 Chestnut St., Philadelphia, PA, 19104, USA. fleming@drexel.edu.ORCID 0000-0002-9637-0246

Funding

New Directions in Sustainable Open-Shell Radical C-C Bond Formations Enabled by Merging Modern Computational and Experimental MethodsR35GM137797 · NIGMS · UNIV OF MARYLAND, COLLEGE PARK · PI Osvaldo Gutierrez · 2020 to 2026
$2.7M
NIGMS NIH HHS R35 GM137797
6 · The paper itself

Abstract

A dearomatization-dislocation-coupling cascade rapidly transforms aromatic isocyanides into highly functionalized cyclohexadienes. The facile cascade installs an exceptional degree of molecular complexity: three carbon-carbon bonds, two quaternary stereocenters, and three orthogonal functionalities, a cyclohexadiene, a nitrile, and an isocyanide. The tolerance of arylisocyanides makes the method among the mildest dearomatizations ever reported, typically occurring within minutes at -78 °C. Experimental and computational analyses implicate an electron transfer-initiated mechanism involving an unprecedented isocyanide rearrangement followed by radical-radical anion coupling. The dearomatization is fast, proceeds via a complex cascade mechanism supported by experimental and computational insight, and provides complex, synthetically valuable cyclohexadienes.

Indexed as

CyanidesCyclohexenesCarbonNitrilesCarbonCyanidesCyclohexenesNitriles

Identifiers

PMID36307409
PMCPMC9616822

What Socratic holds

Textmetadata
LicenceCC BY
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 Socratic graph.