Evidence map›Paper›PMID 36840940›Full record

ArticleAngewandte Chemie (International ed. in English)2023

Practical and General Alcohol Deoxygenation Protocol.

Oliver P Williams, Alyah F Chmiel, Myriam Mikhael, Desiree M Bates, Charles S Yeung, Zachary K Wickens

Open access · hybridAbstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.

0numbers the graph read from it
0cells of the map it votes in
20citing papers in PubMed
11.5field-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

20 citing papers in PubMed, 77 citations in OpenAlex.

  1. Article
  2. Article
  3. Article
  4. Article
  5. Article
  6. Harnessing COJournal of the American Chemical Society · 2026
    Article
  7. Article
  8. Synthesis of depressin, cryptomeridiol and 4-Beilstein journal of organic chemistry · 2026
    Article
  9. Electrochemical Deoxygenative Silylation of Alcohols.Angewandte Chemie (International ed. in English) · 2025
    Article
  10. Article
  11. Article
  12. Article
  13. Article
  14. Article
  15. Single electron reduction of NHC-COChemical science · 2024
    Article
  16. Article
  17. Article
  18. Mechanisms for radical reactions initiating fromBeilstein journal of organic chemistry · 2024
    Article
  19. Review
  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

6 authors at 2 institutions in 1 country.

Oliver P WilliamsDepartment of Chemistry, University of Wisconsin-Madison, Madison, WI-53706, USA.ORCID http://orcid.org/0000-0002-3897-6426
Alyah F ChmielDepartment of Chemistry, University of Wisconsin-Madison, Madison, WI-53706, USA.ORCID http://orcid.org/0000-0002-4859-6689
Myriam MikhaelDiscovery Chemistry, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, MA-02115, USA.ORCID http://orcid.org/0000-0003-4895-6119
Desiree M BatesDepartment of Chemistry, University of Wisconsin-Madison, Madison, WI-53706, USA.ORCID http://orcid.org/0000-0001-9154-2021
Charles S YeungDiscovery Chemistry, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, MA-02115, USA.ORCID http://orcid.org/0000-0001-7320-7190
Zachary K WickensDepartment of Chemistry, University of Wisconsin-Madison, Madison, WI-53706, USA.ORCID http://orcid.org/0000-0002-5733-5288
University of Wisconsin–Madison · USMerck & Co., Inc., Rahway, NJ, USA (United States) · US

Funding

New precursors for diverse radical reactions enabled by potent photoreductantsR01GM146063 · NIGMS · UNIVERSITY OF WISCONSIN-MADISON · PI Zachary Kimble Wickens · 2022 to 2026
$1.5M
Laser-Enhanced NMR Instrumentation for Chemical and Biochemical ResearchS10OD012245 · OD · UNIVERSITY OF WISCONSIN-MADISON · PI CAVAGNERO, SILVIA · 2013 to 2013
$1.0M
QExactive (Orbitrap) mass spectrometerS10OD020022 · OD · UNIVERSITY OF WISCONSIN-MADISON · PI VESTLING, MARTHA M · 2015 to 2015
$483k
NIGMS NIH HHS R01 GM146063NIH HHS 1R01GM146063-01NIH HHS S10 OD012245NIH HHS S10 OD020022
6 · The paper itself

Abstract

Herein, we describe a practical protocol for the removal of alcohol functional groups through reductive cleavage of their benzoate ester analogs. This transformation requires a strong single electron transfer (SET) reductant and a means to accelerate slow fragmentation following substrate reduction. To accomplish this, we developed a photocatalytic system that generates a potent reductant from formate salts alongside Brønsted or Lewis acids that promote fragmentation of the reduced intermediate. This deoxygenation procedure is effective across structurally and electronically diverse alcohols and enables a variety of difficult net transformations. This protocol requires no precautions to exclude air or moisture and remains efficient on multigram scale. Finally, the system can be adapted to a one-pot benzoylation-deoxygenation sequence to enable direct alcohol deletion. Mechanistic studies validate that the role of acidic additives is to promote the key C(sp

Indexed as

DeoxygenationFormateMesolytic CleavagePhotoredox CatalysisReduction

Identifiers

PMID36840940
PMCPMC10121858
OpenAlexW4321996757

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.