Evidence map›Paper›PMID 27121395›Full record

ArticleJournal of the American Chemical Society2016

Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids.

Jeffrey S Bandar, Erhad Ascic, Stephen L Buchwald

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 38 papers.

0numbers the graph read from it
0cells of the map it votes in
38citing papers in PubMed
9.7field-weighted citation impact, top 2% 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

38 citing papers in PubMed, 119 citations in OpenAlex.

  1. Article
  2. Article
  3. Article
  4. Article
  5. Light-Driven Enantioselective Carbene-Catalyzed Radical-Radical Coupling.Angewandte Chemie (International ed. in English) · 2023
    Article
  6. Article
  7. Article
  8. Asymmetric benzylic C(spNature communications · 2021
    Article
  9. Article
  10. Review
  11. Enantioselective C(spNature chemistry · 2021
    Article
  12. Article
  13. Article
  14. Article
  15. Article
  16. Article
  17. Article
  18. Article
  19. Article
  20. 2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines.Synlett : accounts and rapid communications in synthetic organic chemistry · 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 at 1 institution in 1 country.

Jeffrey S BandarDepartment of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
Erhad AscicDepartment of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
Stephen L BuchwaldDepartment of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
Massachusetts Institute of Technology · US

Funding

CATALYTIC METHODS FOR ORGANIC SYNTHESISR37GM046059 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI BUCHWALD, STEPHEN L · 2000 to 2009
$8.1M
EARLY TRANSITION METAL CATALYSTS IN ORGANIC SYNTHESISR01GM046059 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI BUCHWALD, STEPHEN L · 1992 to 2016
$5.4M
Direct Synthesis of 1_2_Benzisoxazoles Via Palladium CatalysisF32GM112197 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI BANDAR, JEFFREY S · 2014 to 2017
$152k
NIGMS NIH HHS F32 GM112197NIGMS NIH HHS R01 GM046059NIGMS NIH HHS R37 GM046059
6 · The paper itself

Abstract

A new method for the enantioselective reductive coupling of aryl alkenes with activated carboxylic acid derivatives via copper hydride catalysis is described. Dual catalytic cycles are proposed, with a relatively fast enantioselective hydroacylation cycle followed by a slower diastereoselective ketone reduction cycle. Symmetrical aryl carboxyclic anhydrides provide access to enantioenriched α-substituted ketones or alcohols with excellent stereoselectivity and functional group tolerance.

Indexed as

AlcoholsAlkenesAnhydridesCarboxylic AcidsCatalysisCopperHeterocyclic CompoundsKetonesMagnetic Resonance SpectroscopyOxidation-ReductionStereoisomerismStyrenesAlcoholsAlkenesAnhydridesCarboxylic AcidsCopperHeterocyclic CompoundsKetonesStyrenes

Identifiers

PMID27121395
PMCPMC4866599
OpenAlexW2343287953

What OpenQuestion holds

Textmetadata
Read underepoch 390

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.