Evidence map›Paper›PMID 33520153›Full record

ReviewChemical science2020

Catalytic hydrogen atom transfer to alkenes: a roadmap for metal hydrides and radicals.

Sophia L Shevick, Conner V Wilson, Simona Kotesova, Dongyoung Kim, Patrick L Holland, Ryan A Shenvi

Abstract readReview
In one paragraph

Review in Chemical science, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 89 papers.

0numbers the graph read from it
0cells of the map it votes in
89citing 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

89 citing papers in PubMed.

  1. Article
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  8. Quaternary Carbons from Amines and Acids.Journal of the American Chemical Society · 2026
    Article
  9. Asymmetric Reduction of Unactivated Alkenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026
    Review
  10. Article
  11. Article
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  15. Article
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  18. Review
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  20. Article

29 more citing papers are in PubMed but not listed here.

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

6 authors.

Sophia L ShevickDepartment of Chemistry , Scripps Research , 10550 North Torrey Pines Road , La Jolla , CA 92037 , USA.ORCID 0000-0003-1703-5448
Conner V WilsonDepartment of Chemistry , Yale University , 225 Prospect St. , New Haven , CT 06511 , USA.
Simona KotesovaDepartment of Chemistry , Scripps Research , 10550 North Torrey Pines Road , La Jolla , CA 92037 , USA.
Dongyoung KimDepartment of Chemistry , Yale University , 225 Prospect St. , New Haven , CT 06511 , USA.
Patrick L HollandDepartment of Chemistry , Yale University , 225 Prospect St. , New Haven , CT 06511 , USA.ORCID 0000-0002-2883-2031
Ryan A ShenviDepartment of Chemistry , Scripps Research , 10550 North Torrey Pines Road , La Jolla , CA 92037 , USA.ORCID 0000-0001-8353-6449

Funding

Unusual Pharmacophores and New Tools for Cross-CouplingR35GM122606 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI Ryan Ashok Shenvi · 2017 to 2026
$7.1M
Mechanistically guided improvement in radical alkene coupling by base metal catalystsR01GM129081 · NIGMS · YALE UNIVERSITY · PI HOLLAND, PATRICK L · 2019 to 2022
$1.2M
NRSA Training CoreTL1TR002551 · NCATS · SCRIPPS RESEARCH INSTITUTE, THE · PI TEYTON, LUC · 2018 to 2022
$1.2M
NCATS NIH HHS TL1 TR002551NIGMS NIH HHS R01 GM129081NIGMS NIH HHS R35 GM122606
6 · The paper itself

Abstract

Hydrogen atom transfer from a metal hydride (MHAT) has emerged as a powerful, if puzzling, technique in chemical synthesis. In catalytic MHAT reactions, earth-abundant metal complexes generate stabilized and unstabilized carbon-centered radicals from alkenes of various substitution patterns with robust chemoselectivity. This perspective combines organic and inorganic perspectives to outline challenges and opportunities, and to propose working models to assist further developments. We attempt to demystify the putative intermediates, the basic elementary steps, and the energetic implications, especially for cage pair formation, collapse and separation. Distinctions between catalysts with strong-field (SF) and weak-field (WF) ligand environments may explain some differences in reactivity and selectivity, and provide an organizing principle for kinetics that transcends the typical thermodynamic analysis. This blueprint should aid practitioners who hope to enter and expand this exciting area of chemistry.

Identifiers

PMID33520153
PMCPMC7810138

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.