Evidence map›Paper›PMID 33660996›Full record

ArticleJournal of the American Chemical Society2021

Photochemical C-H Activation Enables Nickel-Catalyzed Olefin Dicarbofunctionalization.

Mark W Campbell, Mingbin Yuan, Viktor C Polites, Osvaldo Gutierrez, Gary A Molander

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 42 papers.

0numbers the graph read from it
0cells of the map it votes in
42citing papers in PubMed
–field-weighted citation impact
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

42 citing papers in PubMed.

  1. Article
  2. Nickel-Catalyzed Twofold Conjunctive Coupling via Philicity-Alternating Radical Relay.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026
    Article
  3. Article
  4. Article
  5. Article
  6. Article
  7. COAdvanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025
    Article
  8. Article
  9. Article
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  11. Review
  12. Article
  13. Article
  14. Article
  15. Article
  16. Article
  17. Selective C(spNature communications · 2023
    Article
  18. Review
  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

5 authors.

Mark W CampbellRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
Mingbin YuanDepartment of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, United States.
Viktor C PolitesRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
Osvaldo GutierrezDepartment of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, United States.ORCID 0000-0001-8151-7519
Gary A MolanderRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.ORCID 0000-0002-9114-5584

Funding

New Directions in Sustainable Open-Shell Radical C-C Bond Formations Enabled by Merging Modern Computational and Experimental MethodsR35GM137797 · NIGMS · UNIV OF MARYLAND, COLLEGE PARK · PI Osvaldo Gutierrez · 2020 to 2026
$2.7M
Accessing New Chemical Space via Organic SynthesisR35GM131680 · NIGMS · UNIVERSITY OF PENNSYLVANIA · PI MOLANDER, GARY A · 2019 to 2022
$2.4M
Computational Methods for Selective CatalysisR01GM087605 · NIGMS · UNIVERSITY OF PENNSYLVANIA · PI KOZLOWSKI, MARISA C · 2010 to 2019
$2.4M
Targeting Nucleic Acid Junctions with Small MoleculesR01GM118510 · NIGMS · UNIVERSITY OF PENNSYLVANIA · PI CHENOWETH, DAVID MICHAEL · 2016 to 2020
$1.6M
NIGMS NIH HHS R01 GM087605NIGMS NIH HHS R01 GM118510NIGMS NIH HHS R35 GM131680NIGMS NIH HHS R35 GM137797
6 · The paper itself

Abstract

Alkenes, ethers, and alcohols account for a significant percentage of bulk reagents available to the chemistry community. The petrochemical, pharmaceutical, and agrochemical industries each consume gigagrams of these materials as fuels and solvents each year. However, the utilization of such materials as building blocks for the construction of complex small molecules is limited by the necessity of prefunctionalization to achieve chemoselective reactivity. Herein, we report the implementation of efficient, sustainable, diaryl ketone hydrogen-atom transfer (HAT) catalysis to activate native C-H bonds for multicomponent dicarbofunctionalization of alkenes. The ability to forge new carbon-carbon bonds between reagents typically viewed as commodity solvents provides a new, more atom-economic outlook for organic synthesis. Through detailed experimental and computational investigation, the critical effect of hydrogen bonding on the reactivity of this transformation was uncovered.

Indexed as

AlkenesCarbonCatalysisHydrogenHydrogen BondingNickelQuantum TheoryAlkenesCarbonHydrogenNickel

Identifiers

PMID33660996
PMCPMC8012054

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.