Evidence map›Paper›PMID 29490112›Full record

ArticleAngewandte Chemie (International ed. in English)2018

Selective Hydrogen Atom Abstraction through Induced Bond Polarization: Direct α-Arylation of Alcohols through Photoredox, HAT, and Nickel Catalysis.

Jack Twilton, Melodie Christensen, Daniel A DiRocco, Rebecca T Ruck, Ian W Davies, David W C MacMillan

Open access · greenAbstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2018. 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
11.1field-weighted citation impact, top 1% 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

42 citing papers in PubMed, 211 citations in OpenAlex.

  1. Article
  2. COAdvanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025
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  11. Review
  12. Oxetane Synthesis via Alcohol C-H Functionalization.Journal of the American Chemical Society · 2023
    Article
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  14. Variable structure diversification by multicatalysis: the case of alcohols.Chemical communications (Cambridge, England) · 2023
    Review
  15. Article
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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 at 2 institutions in 1 country.

Jack TwiltonMerck Center for Catalysis at Princeton University, Washington Road, Princeton, NJ, 08544, USA.ORCID 0000-0003-3500-4901
Melodie ChristensenProcess Research and Development, MRL, Merck Sharp & Dohme Corp., Rahway, NJ, 07065, USA.
Daniel A DiRoccoProcess Research and Development, MRL, Merck Sharp & Dohme Corp., Rahway, NJ, 07065, USA.
Rebecca T RuckProcess Research and Development, MRL, Merck Sharp & Dohme Corp., Rahway, NJ, 07065, USA.
Ian W DaviesProcess Research and Development, MRL, Merck Sharp & Dohme Corp., Rahway, NJ, 07065, USA.
David W C MacMillanMerck Center for Catalysis at Princeton University, Washington Road, Princeton, NJ, 08544, USA.ORCID 0000-0001-6447-0587
Merck & Co., Inc., Rahway, NJ, USA (United States) · USPrinceton University · US

Funding

Synergistic Catalysis for Chemical SynthesisR01GM103558 · NIGMS · PRINCETON UNIVERSITY · PI MACMILLAN, DAVID W · 2012 to 2019
$2.7M
NIGMS NIH HHS R01 GM103558
6 · The paper itself

Abstract

The combination of nickel metallaphotoredox catalysis, hydrogen atom transfer catalysis, and a Lewis acid activation mode, has led to the development of an arylation method for the selective functionalization of alcohol α-hydroxy C-H bonds. This approach employs zinc-mediated alcohol deprotonation to activate α-hydroxy C-H bonds while simultaneously suppressing C-O bond formation by inhibiting the formation of nickel alkoxide species. The use of Zn-based Lewis acids also deactivates other hydridic bonds such as α-amino and α-oxy C-H bonds. This approach facilitates rapid access to benzylic alcohols, an important motif in drug discovery. A 3-step synthesis of the drug Prozac exemplifies the utility of this new method.

Indexed as

alcoholsheterocycleshydrogen atom transfernickelphotoredox catalysis

Identifiers

PMID29490112
PMCPMC6448405
OpenAlexW2793744510

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.