Evidence map›Paper›PMID 38033883›Full record

ArticleChemical science2023

Kinetically-driven reactivity of sulfinylamines enables direct conversion of carboxylic acids to sulfinamides.

Hang T Dang, Arka Porey, Sachchida Nand, Ramon Trevino, Patrick Manning-Lorino, William B Hughes, Seth O Fremin, William T Thompson, Shree Krishna Dhakal, Hadi D Arman and 1 more

Abstract read
In one paragraph

Article in Chemical science, 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.

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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

11 authors.

Hang T DangDepartment of Chemistry, The University of Texas at San Antonio One UTSA Circle San Antonio TX 78249 USA oleg.larionov@utsa.edu.ORCID https://orcid.org/0000-0003-2517-7163
Arka PoreyDepartment of Chemistry, The University of Texas at San Antonio One UTSA Circle San Antonio TX 78249 USA oleg.larionov@utsa.edu.
Sachchida NandDepartment of Chemistry, The University of Texas at San Antonio One UTSA Circle San Antonio TX 78249 USA oleg.larionov@utsa.edu.
Ramon TrevinoDepartment of Chemistry, The University of Texas at San Antonio One UTSA Circle San Antonio TX 78249 USA oleg.larionov@utsa.edu.
Patrick Manning-LorinoDepartment of Chemistry, The University of Texas at San Antonio One UTSA Circle San Antonio TX 78249 USA oleg.larionov@utsa.edu.
William B HughesDepartment of Chemistry, The University of Texas at San Antonio One UTSA Circle San Antonio TX 78249 USA oleg.larionov@utsa.edu.
Seth O FreminDepartment of Chemistry, The University of Texas at San Antonio One UTSA Circle San Antonio TX 78249 USA oleg.larionov@utsa.edu.
William T ThompsonDepartment of Chemistry, The University of Texas at San Antonio One UTSA Circle San Antonio TX 78249 USA oleg.larionov@utsa.edu.
Shree Krishna DhakalDepartment of Chemistry, The University of Texas at San Antonio One UTSA Circle San Antonio TX 78249 USA oleg.larionov@utsa.edu.
Hadi D ArmanDepartment of Chemistry, The University of Texas at San Antonio One UTSA Circle San Antonio TX 78249 USA oleg.larionov@utsa.edu.
Oleg V LarionovDepartment of Chemistry, The University of Texas at San Antonio One UTSA Circle San Antonio TX 78249 USA oleg.larionov@utsa.edu.ORCID https://orcid.org/0000-0002-3026-1135

Funding

UTSA RISE Research Training ProgramR25GM060655 · NIGMS · UNIVERSITY OF TEXAS SAN ANTONIO · PI BAREA-RODRIGUEZ, EDWIN J · 2000 to 2022
$21.6M
New organosulfur-based strategies for efficient and selective organic synthesis.R01GM134371 · NIGMS · UNIVERSITY OF TEXAS SAN ANTONIO · PI LARIONOV, OLEG V · 2019 to 2022
$1.1M
NIGMS NIH HHS R01 GM134371NIGMS NIH HHS R25 GM060655
6 · The paper itself

Abstract

Sulfinamides are some of the most centrally important four-valent sulfur compounds that serve as critical entry points to an array of emergent medicinal functional groups, molecular tools for bioconjugation, and synthetic intermediates including sulfoximines, sulfonimidamides, and sulfonimidoyl halides, as well as a wide range of other S(iv) and S(vi) functionalities. Yet, the accessible chemical space of sulfinamides remains limited, and the approaches to sulfinamides are largely confined to two-electron nucleophilic substitution reactions. We report herein a direct radical-mediated decarboxylative sulfinamidation that for the first time enables access to sulfinamides from the broad and structurally diverse chemical space of carboxylic acids. Our studies show that the formation of sulfinamides prevails despite the inherent thermodynamic preference for the radical addition to the nitrogen atom, while a machine learning-derived model facilitates prediction of the reaction efficiency based on computationally generated descriptors of the underlying radical reactivity.

Identifiers

PMID38033883
PMCPMC10685282

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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.