Evidence map›Paper›PMID 27305062›Full record

ArticleAngewandte Chemie (International ed. in English)2016

Highly Stereoselective Cobalt(III)-Catalyzed Three-Component C-H Bond Addition Cascade.

Jeffrey A Boerth, Joshua R Hummel, Jonathan A Ellman

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.

0numbers the graph read from it
0cells of the map it votes in
23citing papers in PubMed
24.6field-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

23 citing papers in PubMed, 169 citations in OpenAlex.

  1. Article
  2. Article
  3. Review
  4. Article
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  7. Article
  8. Direct Preparation ofThe Journal of organic chemistry · 2021
    Article
  9. Article
  10. Review
  11. Article
  12. Asymmetric Mannich reactions of (Beilstein journal of organic chemistry · 2020
    Article
  13. Synthesis of Homoallylic Alcohols with Acyclic Quaternary Centers through CoAngewandte Chemie (International ed. in English) · 2019
    Article
  14. Review
  15. Article
  16. Article
  17. Hydroarylations by cobalt-catalyzed C-H activation.Beilstein journal of organic chemistry · 2018
    Review
  18. Convergent Synthesis ofIsrael journal of chemistry · 2017
    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

3 authors at 1 institution in 1 country.

Jeffrey A BoerthDepartment of Chemistry, Yale University, 225 Prospect St., New Haven, CT, 06520, USA.
Joshua R HummelDepartment of Chemistry, Yale University, 225 Prospect St., New Haven, CT, 06520, USA.
Jonathan A EllmanDepartment of Chemistry, Yale University, 225 Prospect St., New Haven, CT, 06520, USA. jonathan.ellman@yale.edu.ORCID 0000-0001-9320-5512
Yale University · US

Funding

Yale Clinical and Translational Science Award (U Component)UL1TR001863 · NCATS · YALE UNIVERSITY · PI John H. Krystal, LUCILA OHNO-MACHADO · 2016 to 2026
$102.9M
C-H Functionalization for the Synthesis of Amines and Nitrogen HeterocyclesR01GM069559 · NIGMS · YALE UNIVERSITY · PI ELLMAN, JONATHAN A · 2004 to 2017
$5.4M
NCATS NIH HHS UL1 TR001863NIGMS NIH HHS R01 GM069559
6 · The paper itself

Abstract

A highly stereoselective three-component C(sp(2) )-H bond addition across alkene and polarized π-bonds is reported for which Co(III) catalysis was shown to be much more effective than Rh(III) . The reaction proceeds at ambient temperature with both aryl and alkyl enones employed as efficient coupling partners. Moreover, the reaction exhibits extremely broad scope with respect to the aldehyde input; electron rich and poor aromatic, alkenyl, and branched and unbranched alkyl aldehydes all couple in good yield and with high diastereoselectivity. Multiple directing groups participate in this transformation, including pyrazole, pyridine, and imine functional groups. Both aromatic and alkenyl C(sp(2) )-H bonds undergo the three-component addition cascade, and the alkenyl addition product can readily be converted into diastereomerically pure five-membered lactones. Additionally, the first asymmetric reactions with Co(III) -catalyzed C-H functionalization are demonstrated with three-component C-H bond addition cascades employing N-tert-butanesulfinyl imines. These examples represent the first transition metal catalyzed C-H bond additions to N-tert-butanesulfinyl imines, which are versatile and extensively used intermediates for the asymmetric synthesis of amines.

Indexed as

AldehydesAminesCatalysisCobaltIminesMolecular StructurePyrazolesPyridinesStereoisomerismAldehydesAminesCobaltIminespyrazolePyrazolespyridinePyridinesC−H activationdiastereoselectivityhomogeneous catalysismulticomponent reactions

Identifiers

PMID27305062
PMCPMC5039075
OpenAlexW2421354436

What OpenQuestion holds

Textmetadata
LicenceTDM
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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.