Evidence map›Paper›PMID 30650228›Full record

ArticleAngewandte Chemie (International ed. in English)2019

Enantioconvergent Cross-Couplings of Alkyl Electrophiles: The Catalytic Asymmetric Synthesis of Organosilanes.

Gregg M Schwarzwalder, Carson D Matier, Gregory C Fu

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.

0numbers the graph read from it
0cells of the map it votes in
17citing 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

17 citing papers in PubMed.

  1. Review
  2. Article
  3. Article
  4. CFNature communications · 2025
    Article
  5. Article
  6. Ni(2,2':6',2''-terpyridine)Dalton transactions (Cambridge, England : 2003) · 2024
    Article
  7. Article
  8. Review
  9. Article
  10. Article
  11. Article
  12. Enantio- and Regioconvergent Nickel-Catalyzed C(spAngewandte Chemie (International ed. in English) · 2021
    Article
  13. Review
  14. Article
  15. Article
  16. Article
  17. Photochemical Asymmetric Nickel-Catalyzed Acyl Cross-Coupling.Angewandte Chemie (International ed. in English) · 2019
    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

3 authors.

Gregg M SchwarzwalderDivision of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA, 91125, USA.
Carson D MatierDivision of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA, 91125, USA.
Gregory C FuDivision of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA, 91125, USA.ORCID 0000-0002-0927-680X

Funding

Metal-Catalyzed Coupling ReactionsR37GM062871 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI FU, GREGORY C · 2010 to 2019
$5.5M
Versatile Methods for Palladium-Catalyzed CouplingsR01GM062871 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI FU, GREGORY C · 2001 to 2022
$5.5M
Nickel-Catalyzed Asymmetric Synthesis of Fully Saturated Nitrogen HeterocyclesF32GM116234 · NIGMS · CALIFORNIA INSTITUTE OF TECHNOLOGY · PI SCHWARZWALDER, GREGG · 2015 to 2017
$107k
NIGMS NIH HHS F32 GM116234NIGMS NIH HHS F32-GM116234NIGMS NIH HHS R01 GM062871NIGMS NIH HHS R01-GM062871NIGMS NIH HHS R37 GM062871
6 · The paper itself

Abstract

Metal-catalyzed enantioconvergent cross-coupling reactions of alkyl electrophiles are emerging as a powerful tool in asymmetric synthesis. To date, high enantioselectivity has been limited to couplings of electrophiles that bear a directing group or a proximal p/π orbital. Herein, we demonstrate for the first time that enantioconvergent cross-couplings can be achieved with electrophiles that lack such features; specifically, we establish that a chiral nickel catalyst can accomplish Negishi reactions of racemic α-halosilanes with alkylzinc reagents with good enantioselectivity under simple and mild conditions, thereby providing access to enantioenriched organosilanes, an important class of target molecules.

Indexed as

AlkylationCatalysisCoordination ComplexesMolecular StructureNickelOrganosilicon CompoundsStereoisomerismZinc CompoundsCoordination ComplexesNickelOrganosilicon CompoundsZinc Compoundsalkylationasymmetric catalysiscross-couplingnickelsilicon

Identifiers

PMID30650228
PMCPMC6399024

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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.