Evidence map›Paper›PMID 36440659›Full record

ArticleAngewandte Chemie (International ed. in English)2023

Metal-Free Intermolecular C-H Borylation of N-Heterocycles at B-B Multiple Bonds.

Tobias Brückner, Benedikt Ritschel, J Oscar C Jiménez-Halla, Felipe Fantuzzi, Dario Duwe, Christian Markl, Rian D Dewhurst, Maximilian Dietz, Holger Braunschweig

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2023. 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. Metal-Free Intermolecular C-H Borylation of N-Heterocycles at B-B Multiple Bonds.Angewandte Chemie (International ed. in English) · 2023
    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

9 authors.

Tobias BrücknerInstitute for Inorganic Chemistry, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
Benedikt RitschelInstitute for Inorganic Chemistry, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
J Oscar C Jiménez-HallaDepartment of Chemistry, Division of Natural and Exact, 36050, Guanajuato, Mexico.ORCID http://orcid.org/0000-0001-7354-3506
Felipe FantuzziSchool of Chemistry and Forensic Science, University of Kent, Park Wood Rd, Canterbury, CT2 7NH, UK.ORCID http://orcid.org/0000-0002-8200-8262
Dario DuweInstitute for Inorganic Chemistry, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
Christian MarklInstitute for Inorganic Chemistry, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
Rian D DewhurstInstitute for Inorganic Chemistry, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.ORCID http://orcid.org/0000-0001-5978-811X
Maximilian DietzInstitute for Inorganic Chemistry, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
Holger BraunschweigInstitute for Inorganic Chemistry, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.ORCID http://orcid.org/0000-0001-9264-1726

Funding

Alexander von Humboldt-StiftungCoordenação de Aperfeiçoamento de Pessoal de Nível SuperiorDeutsche Forschungsgemeinschaft 466754611H2020 European Research Council 669054
6 · The paper itself

Abstract

Carbene-stabilized diborynes of the form LBBL (L=N-heterocyclic carbene (NHC) or cyclic alkyl(amino)carbene (CAAC)) induce rapid, high yielding, intermolecular ortho-C-H borylation at N-heterocycles at room temperature. A simple pyridyldiborene is formed when an NHC-stabilized diboryne is combined with pyridine, while a CAAC-stabilized diboryne leads to activation of two pyridine molecules to give a tricyclic alkylideneborane, which can be forced to undergo a further H-shift resulting in a zwitterionic, doubly benzo-fused 1,3,2,5-diazadiborinine by heating. Use of the extended N-heteroaromatic quinoline leads to a borylmethyleneborane under mild conditions via an unprecedented boron-carbon exchange process.

Indexed as

BoronBorylationCarbeneDiboryneHydroarylation

Identifiers

PMID36440659
PMCPMC10107673

What OpenQuestion holds

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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 OpenQuestion graph.