Evidence map›Paper›PMID 32395998›Full record

ArticleJournal of the American Chemical Society2020

Synthesis of Pyrroles through the CuH-Catalyzed Coupling of Enynes and Nitriles.

Yujing Zhou, Lin Zhou, Luke T Jesikiewicz, Peng Liu, Stephen L Buchwald

Open access · greenAbstract read
In one paragraph

Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.

0numbers the graph read from it
0cells of the map it votes in
11citing papers in PubMed
5.6field-weighted citation impact, top 3% 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

11 citing papers in PubMed, 87 citations in OpenAlex.

  1. Building Crosslinking Network via Catalytic Furan-to-Pyrrole Conversion.Angewandte Chemie (International ed. in English) · 2026
    Article
  2. Article
  3. Review
  4. Article
  5. Green Synthesis of Bioactive Pyrrole DerivativesCurrent topics in medicinal chemistry · 2025
    Review
  6. Recent Advances in Synthetic Routes to Azacycles.Molecules (Basel, Switzerland) · 2023
    Review
  7. Article
  8. Article
  9. Article
  10. Review
  11. Review
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

5 authors at 2 institutions in 1 country.

Yujing ZhouDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.ORCID 0000-0002-8161-8560
Lin ZhouDepartment of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.
Luke T JesikiewiczDepartment of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.
Peng LiuDepartment of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.ORCID 0000-0002-8188-632X
Stephen L BuchwaldDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.ORCID 0000-0003-3875-4775
University of Pittsburgh · USMassachusetts Institute of Technology · US

Funding

Metal-Catalyzed Methods for Organic SynthesisR35GM122483 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI STEPHEN L BUCHWALD · 2017 to 2026
$11.4M
Computational Models for Reactivity and Selectivity in Transition Metal-Catalyzed Olefin FunctionalizationR35GM128779 · NIGMS · UNIVERSITY OF PITTSBURGH AT PITTSBURGH · PI Peng Liu · 2018 to 2026
$2.9M
NIGMS NIH HHS R35 GM122483NIGMS NIH HHS R35 GM128779
6 · The paper itself

Abstract

Herein, we describe an efficient method to prepare polysubstituted pyrroles via a copper hydride (CuH)-catalyzed enyne-nitrile coupling reaction. This protocol accommodates both aromatic and aliphatic substituents and a broad range of functional groups, providing a variety of N-H pyrroles in good yields and with high regioselectivity. We propose that the Cu-based catalyst promotes both the initial reductive coupling and subsequent cyclization steps. Density functional theory (DFT) calculations were performed to elucidate the reaction mechanism.

Indexed as

AlkynesCatalysisCopperHydrogenMolecular StructureNitrilesPyrrolesAlkynesCopperHydrogenNitrilesPyrroles

Identifiers

PMID32395998
PMCPMC8009196
OpenAlexW3025996521

What OpenQuestion holds

Textmetadata
LicenceTDM
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.