Evidence map›Paper›PMID 29260868›Full record

ArticleJournal of the American Chemical Society2018

Migratory Insertion of Carbenes into Au(III)-C Bonds.

Aleksandr V Zhukhovitskiy, Ilia J Kobylianskii, Chung-Yeh Wu, F Dean Toste

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.

0numbers the graph read from it
0cells of the map it votes in
8citing papers in PubMed
1.8field-weighted citation impact, top 15% 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

8 citing papers in PubMed, 47 citations in OpenAlex.

  1. Article
  2. Article
  3. Migratory Insertion of CO into a Au-C Bond.Journal of the American Chemical Society · 2022
    Article
  4. Article
  5. Article
  6. Article
  7. Article
  8. A Dinuclear Mechanism Implicated in Controlled Carbene Polymerization.Journal of the American Chemical Society · 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

4 authors at 1 institution in 1 country.

Aleksandr V ZhukhovitskiyDepartment of Chemistry, University of California , Berkeley, California 94720, United States.ORCID 0000-0002-3873-4179
Ilia J KobylianskiiDepartment of Chemistry, University of California , Berkeley, California 94720, United States.
Chung-Yeh WuDepartment of Chemistry, University of California , Berkeley, California 94720, United States.
F Dean TosteDepartment of Chemistry, University of California , Berkeley, California 94720, United States.ORCID 0000-0001-8018-2198
University of California, Berkeley · US

Funding

Methods for Selective Organic Synthesis based on Ionic CatalystsR35GM118190 · NIGMS · UNIVERSITY OF CALIFORNIA BERKELEY · PI F. Dean Toste · 2016 to 2026
$6.7M
High Performance Computing Cluster for Public Health Driven Molecular Science - Core FacilityS10OD023532 · OD · UNIVERSITY OF CALIFORNIA BERKELEY · PI DURKIN, KATHLEEN A · 2017 to 2017
$434k
NIGMS NIH HHS R35 GM118190NIH HHS S10 OD023532
6 · The paper itself

Abstract

Migratory insertion of carbon-based species into transition-metal-carbon bonds is a mechanistic manifold of vast significance: it underlies the Fischer-Tropsch process, Mizoroki-Heck reaction, Ziegler-Natta and analogous late-transition-metal-catalyzed olefin polymerizations, and a number of carbonylative methods for the synthesis of ketones and esters, among others. Although this type of reactivity is well-precedented for most transition metals, gold constitutes a notable exception, with virtually no well-characterized examples known to date. Yet, the complementary reactivity of gold to numerous other transition metals would offer new synthetic opportunities for migratory insertion of carbon-based species into gold-carbon bonds. Here we report the discovery of well-defined Au(III) complexes that participate in rapid migratory insertion of carbenes derived from silyl- or carbonyl-stabilized diazoalkanes into Au-C bonds at temperatures ≥ -40 °C. Through a combined theoretical and experimental approach, key kinetic, thermodynamic, and structural details of this reaction manifold were elucidated. This study paves the way for homogeneous gold-catalyzed processes incorporating carbene migratory insertion steps.

Indexed as

CarbonCatalysisGoldKineticsLigandsMethaneMolecular StructureThermodynamicscarbeneCarbonGoldLigandsMethane

Identifiers

PMID29260868
PMCPMC5765531
OpenAlexW2780500026

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.