Evidence map›Paper›PMID 35186424›Full record

ArticleACS catalysis2021

Identifying the Imperative Role of Metal-Olefin Interactions in Catalytic C-O Reductive Elimination from Nickel(II).

Trevor D Lohrey, Alexander Q Cusumano, William A Goddard, Brian M Stoltz

Open access · greenAbstract read
In one paragraph

Article in ACS catalysis, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.

0numbers the graph read from it
0cells of the map it votes in
3citing papers in PubMed
1.1field-weighted citation impact, top 26% 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

3 citing papers in PubMed, 11 citations in OpenAlex.

  1. Mechanism of Ni-Catalyzed Photochemical Halogen Atom-Mediated C(spJournal of the American Chemical Society · 2024
    Article
  2. Article
  3. 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

4 authors at 1 institution in 1 country.

Trevor D LohreyThe Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
Alexander Q CusumanoThe Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
William A GoddardMaterials and Process Simulation Center, Beckman Institute, California Institute of Technology, Pasadena, California 91125, United States.ORCID 0000-0003-0097-5716
Brian M StoltzThe Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.ORCID 0000-0001-9837-1528
California Institute of Technology · US

Funding

The Synthesis of Bioactive Polycyclic Natural ProductsR01GM080269 · NIGMS · CALIFORNIA INSTITUTE OF TECHNOLOGY · PI STOLTZ, BRIAN M · 2007 to 2022
$5.0M
The Synthesis of Bioactive Natural Products as a Driving Force for Discovery in Organic ChemistryR35GM145239 · NIGMS · CALIFORNIA INSTITUTE OF TECHNOLOGY · PI BRIAN M STOLTZ · 2022 to 2026
$3.1M
NIGMS NIH HHS R01 GM080269NIGMS NIH HHS R35 GM145239
6 · The paper itself

Abstract

We present a series of experimental and computational mechanistic investigations of an unusually facile example of Ni-catalyzed C-O bond formation. Our method, originally reported in 2016, involves the formation of cyclic enol ethers from vinyl iodides bearing pendant alcohol groups. Our findings suggest that the observed reactivity arises from the coordination of the olefin in the vinyl iodide starting material and the enol ether product with Ni(0) intermediates. Density functional theory calculations reveal a plausible catalytic mechanism involving a Ni(II)/Ni(0) redox cycle featuring two-electron C-I oxidative addition and C-O reductive elimination steps. The direct formation of a

Indexed as

computational chemistrycross-couplingenol ethernickelorganometallic chemistryquantum mechanicsreductive eliminationzinc

Identifiers

PMID35186424
PMCPMC8849544
OpenAlexW3193450967

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.