Evidence map›Paper›PMID 31515388›Full record

ArticleScience (New York, N.Y.)2019

Synthesis of a copper-supported triplet nitrene complex pertinent to copper-catalyzed amination.

Kurtis M Carsch, Ida M DiMucci, Diana A Iovan, Alex Li, Shao-Liang Zheng, Charles J Titus, Sang Jun Lee, Kent D Irwin, Dennis Nordlund, Kyle M Lancaster and 1 more

Open access · greenAbstract read
In one paragraph

Article in Science (New York, N.Y.), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 59 papers.

0numbers the graph read from it
0cells of the map it votes in
59citing papers in PubMed
12.8field-weighted citation impact, top 1% of its field
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

59 citing papers in PubMed, 193 citations in OpenAlex.

  1. Article
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  3. Journal of the American Chemical Society · 2026
    Article
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  9. C(spJournal of the American Chemical Society · 2025
    Article
  10. ACS central science · 2025
    Review
  11. An Open-Shell FeJournal of the American Chemical Society · 2025
    Article
  12. Article
  13. Bottleable triplet nitrenes.Nature chemistry · 2025
    Article
  14. Article
  15. C-H Insertion from Isolable Copper Benzylidenes.Journal of the American Chemical Society · 2024
    Article
  16. Article
  17. Article
  18. Article
  19. Article
  20. 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

11 authors at 4 institutions in 1 country.

Kurtis M CarschDepartment of Chemistry and Chemical Biology, Harvard University, Cambridge, MA, USA.ORCID 0000-0003-4432-7518
Ida M DiMucciDepartment of Chemistry and Chemical Biology, Cornell University, Ithaca, NY, USA.ORCID 0000-0003-3440-7856
Diana A IovanDepartment of Chemistry and Chemical Biology, Harvard University, Cambridge, MA, USA.ORCID 0000-0001-9889-7183
Alex LiDepartment of Chemistry and Chemical Biology, Harvard University, Cambridge, MA, USA.ORCID 0000-0001-9912-1643
Shao-Liang ZhengDepartment of Chemistry and Chemical Biology, Harvard University, Cambridge, MA, USA.ORCID 0000-0002-6432-9943
Charles J TitusDepartment of Physics, Stanford University, Stanford, CA, USA.ORCID 0000-0001-6312-8552
Sang Jun LeeStanford Synchrotron Radiation Lightsource, SLAC National Accelerator Laboratory, Menlo Park, CA, USA.ORCID 0000-0002-8199-3993
Kent D IrwinDepartment of Physics, Stanford University, Stanford, CA, USA.ORCID 0000-0002-2998-9743
Dennis NordlundStanford Synchrotron Radiation Lightsource, SLAC National Accelerator Laboratory, Menlo Park, CA, USA.ORCID 0000-0001-9524-6908
Kyle M LancasterDepartment of Chemistry and Chemical Biology, Cornell University, Ithaca, NY, USA. betley@chemistry.harvard.edu kml236@cornell.edu.ORCID 0000-0001-7296-128X
Theodore A BetleyDepartment of Chemistry and Chemical Biology, Harvard University, Cambridge, MA, USA. betley@chemistry.harvard.edu kml236@cornell.edu.ORCID 0000-0001-5946-9629
Harvard University · USSLAC National Accelerator Laboratory · USCornell University · USStanford University · US

Funding

X-ray Absorption Spectroscopy (XAS) pp.711-759P41GM103393 · NIGMS · STANFORD UNIVERSITY · PI HODGSON, KEITH O · 2012 to 2019
$30.6M
Correlation of electronic structure to iron catalyzed C-H bond functionalizationR01GM115815 · NIGMS · HARVARD UNIVERSITY · PI BETLEY, THEODORE A · 2015 to 2018
$1.3M
NIGMS NIH HHS P41 GM103393NIGMS NIH HHS R01 GM115815
6 · The paper itself

Abstract

Terminal copper-nitrenoid complexes have inspired interest in their fundamental bonding structures as well as their putative intermediacy in catalytic nitrene-transfer reactions. Here, we report that aryl azides react with a copper(I) dinitrogen complex bearing a sterically encumbered dipyrrin ligand to produce terminal copper nitrene complexes with near-linear, short copper-nitrenoid bonds [1.745(2) to 1.759(2) angstroms]. X-ray absorption spectroscopy and quantum chemistry calculations reveal a predominantly triplet nitrene adduct bound to copper(I), as opposed to copper(II) or copper(III) assignments, indicating the absence of a copper-nitrogen multiple-bond character. Employing electron-deficient aryl azides renders the copper nitrene species competent for alkane amination and alkene aziridination, lending further credence to the intermediacy of this species in proposed nitrene-transfer mechanisms.

Identifiers

PMID31515388
PMCPMC7256962
OpenAlexW2973065635

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.