Evidence map›Paper›PMID 39196314›Full record

ArticleJournal of the American Chemical Society2024

Cu-Catalyzed Three-Component Alkene Carboamination: Mechanistic Insights and Rational Design to Overcome Limitations.

Tam D Ho, Byung Joo Lee, Travis L Buchanan, Micah E Heikes, Ryan M Steinert, E Grace Milem, Sean T Goralski, Ya-Nong Wang, SangHyun Lee, Vincent M Lynch and 3 more

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Journal of the American Chemical Society, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.

0numbers the graph read from it
0cells of the map it votes in
5citing 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

5 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

13 authors.

Tam D HoDepartment of Chemistry, University of Texas at Austin, 100 East 24th Street, Austin, Texas, 78712, United States.
Byung Joo LeeDepartment of Chemistry, University of Texas at Austin, 100 East 24th Street, Austin, Texas, 78712, United States.
Travis L BuchananDepartment of Chemistry, University of Texas at Austin, 100 East 24th Street, Austin, Texas, 78712, United States.
Micah E HeikesDepartment of Chemistry and Biochemistry, Wichita State University, 1845 Fairmount Street, Wichita, Kansas, 67260-0051, United States.
Ryan M SteinertDepartment of Chemistry and Biochemistry, Wichita State University, 1845 Fairmount Street, Wichita, Kansas, 67260-0051, United States.ORCID 0000-0002-2157-6362
E Grace MilemDepartment of Chemistry, University of Texas at Austin, 100 East 24th Street, Austin, Texas, 78712, United States.ORCID 0009-0001-7467-1160
Sean T GoralskiDepartment of Chemistry, University of Texas at Austin, 100 East 24th Street, Austin, Texas, 78712, United States.ORCID 0000-0002-4169-338X
Ya-Nong WangDepartment of Chemistry, University of Texas at Austin, 100 East 24th Street, Austin, Texas, 78712, United States.ORCID 0000-0002-5838-3855
SangHyun LeeDepartment of Chemistry, University of Texas at Austin, 100 East 24th Street, Austin, Texas, 78712, United States.ORCID 0000-0001-9519-137X
Vincent M LynchDepartment of Chemistry, University of Texas at Austin, 100 East 24th Street, Austin, Texas, 78712, United States.
Michael J RoseDepartment of Chemistry, University of Texas at Austin, 100 East 24th Street, Austin, Texas, 78712, United States.ORCID 0000-0002-6960-6639
Katie R Mitchell-KochDepartment of Chemistry and Biochemistry, Wichita State University, 1845 Fairmount Street, Wichita, Kansas, 67260-0051, United States.ORCID 0000-0002-9173-3677
Kami L HullDepartment of Chemistry, University of Texas at Austin, 100 East 24th Street, Austin, Texas, 78712, United States.ORCID 0000-0003-3102-2686

Funding

Transition Metal-Catalyzed Alkene FunctionalizationR35GM125029 · NIGMS · UNIVERSITY OF TEXAS AT AUSTIN · PI Kami Lee Hull · 2017 to 2026
$2.7M
NIGMS NIH HHS R35 GM125029
6 · The paper itself

Abstract

Herein, we report mechanistic investigations into the Cu-catalyzed three-component carboamination of alkenes with α-halo carbonyls and aryl amines via an oxocarbenium intermediate. Monitoring the reaction reveals the formation of transient atom transfer radical addition (ATRA) intermediates with both electron-neutral and deficient vinyl arenes as well as unactivated alkenes. Based on our experimental studies and density functional theory calculations, the oxocarbenium is generated through atom transfer and subsequent intramolecular substitution. Further, mechanistic factors that dictate the regioselectivity of the nucleophilic attack onto the oxocarbenium to afford the γ-amino ester, γ-iminolactone, or γ-lactone are discussed. A strategy to overcome scope limitation with respect to unactivated alkenes is developed using the mechanistic insights gained herein. Finally, we demonstrate that under modified conditions, our Cu catalyst enables the ATRA reaction between a variety of alkyl halides and vinyl arenes/α-olefins, and we present a one-pot, two-step carbofunctionalization with an array of nucleophiles through ATRA/S

Identifiers

PMID39196314
PMCPMC12323559

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