Evidence map›Paper›PMID 37788150›Full record

ArticleJournal of the American Chemical Society2023

An Asymmetric Aromatic Finkelstein Reaction: A Platform for Remote Diarylmethane Desymmetrization.

Tobias Morack, Tyler E Myers, Lucas J Karas, Melissa A Hardy, Brandon Q Mercado, Matthew S Sigman, Scott J Miller

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.

0numbers the graph read from it
0cells of the map it votes in
9citing 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

9 citing papers in PubMed.

  1. Article
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  6. Review
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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.

Tobias MorackDepartment of Chemistry, Yale University, New Haven, Connecticut 06520-8107, United States.ORCID 0000-0003-2045-730X
Tyler E MyersDepartment of Chemistry, Yale University, New Haven, Connecticut 06520-8107, United States.ORCID 0009-0004-6228-4915
Lucas J KarasDepartment of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, United States.ORCID 0000-0001-7970-119X
Melissa A HardyDepartment of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, United States.
Brandon Q MercadoDepartment of Chemistry, Yale University, New Haven, Connecticut 06520-8107, United States.
Matthew S SigmanDepartment of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, United States.ORCID 0000-0002-5746-8830
Scott J MillerDepartment of Chemistry, Yale University, New Haven, Connecticut 06520-8107, United States.ORCID 0000-0001-7817-1318

Funding

Site-Selective Catalysis for Bioactive Scaffold DiversificationR35GM132092 · NIGMS · YALE UNIVERSITY · PI Scott J Miller · 2019 to 2026
$6.3M
Data Science Guided Organic Reaction DevelopmentR35GM136271 · NIGMS · UTAH STATE HIGHER EDUCATION SYSTEM--UNIVERSITY OF UTAH · PI MATTHEW S SIGMAN · 2020 to 2026
$3.5M
NIGMS NIH HHS R35 GM132092NIGMS NIH HHS R35 GM136271
6 · The paper itself

Abstract

A first-of-its-kind enantioselective aromatic Finkelstein reaction is disclosed for the remote desymmetrization of diarylmethanes. The reaction operates through a copper-catalyzed C-I bond-forming event, and high levels of enantioselectivity are achieved through the deployment of a tailored guanidinylated peptide ligand. Strategic use of transition-metal-mediated reactions enables the chemoselective modification of the aryl iodide products; thus, the synthesis of a diverse set of otherwise difficult-to-access diarylmethanes with excellent levels of selectivity is realized from a common intermediate. A mixed experimental/computational analysis of steric parameters and substrate conformations identifies the importance of remote conformational effects as a key to achieving high enantioselectivity in this desymmetrization reaction.

Identifiers

PMID37788150
PMCPMC10591928

What OpenQuestion holds

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Registered trials

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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.