Evidence map›Paper›PMID 36864142›Full record

ArticleNature chemistry2023

Alkyl sulfinates as cross-coupling partners for programmable and stereospecific installation of C(sp

Min Zhou, Jet Tsien, Ryan Dykstra, Jonathan M E Hughes, Byron K Peters, Rohan R Merchant, Osvaldo Gutierrez, Tian Qin

Open access · greenAbstract read
In one paragraph

Article in Nature chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.

0numbers the graph read from it
0cells of the map it votes in
7citing papers in PubMed
4.8field-weighted citation impact, top 4% 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

7 citing papers in PubMed, 32 citations in OpenAlex.

  1. Article
  2. Article
  3. Article
  4. Article
  5. CFJACS Au · 2024
    Article
  6. Three-dimensional saturated C(spNature reviews. Chemistry · 2024
    Review
  7. 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

8 authors at 4 institutions in 1 country.

Min Zhou *Department of Biochemistry, The University of Texas Southwestern Medical Center, Harry Hines Blvd, Dallas, TX, USA.
Jet Tsien *Department of Biochemistry, The University of Texas Southwestern Medical Center, Harry Hines Blvd, Dallas, TX, USA.
Ryan DykstraDepartment of Chemistry and Biochemistry, University of Maryland, College Park, MD, USA.ORCID http://orcid.org/0000-0002-1407-3847
Jonathan M E HughesDepartment of Process Research and Development, Merck & Co., Inc., Rahway, NJ, USA.ORCID http://orcid.org/0000-0002-5708-2882
Byron K PetersDepartment of Process Research and Development, Merck & Co., Inc., Rahway, NJ, USA.
Rohan R MerchantDepartment of Discovery Chemistry, Merck & Co., Inc., South San Francisco, CA, USA.ORCID http://orcid.org/0000-0002-5472-8780
Osvaldo GutierrezDepartment of Chemistry and Biochemistry, University of Maryland, College Park, MD, USA. og.labs@tamu.edu.ORCID http://orcid.org/0000-0001-8151-7519
Tian QinDepartment of Biochemistry, The University of Texas Southwestern Medical Center, Harry Hines Blvd, Dallas, TX, USA. tian.qin@utsouthwestern.edu.ORCID http://orcid.org/0000-0001-7225-3224
Merck & Co., Inc., Rahway, NJ, USA (United States) · USThe University of Texas Southwestern Medical Center · USUniversity of Maryland, College Park · USSouthwestern Medical Center · US

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
Development of Sulfur-Based Reactions with Translational ApplicationsR01GM141088 · NIGMS · UT SOUTHWESTERN MEDICAL CENTER · PI Tian Qin · 2021 to 2026
$2.1M
NIGMS NIH HHS R01 GM141088NIGMS NIH HHS R35 GM137797
6 · The paper itself

Abstract

In recent years, a variety of cycloalkyl groups with quaternary carbons, in particular cyclopropyl and cyclobutyl trifluoromethyl groups, have emerged as promising bioisosteres in drug-like molecules. The modular installation of such bioisosteres remains challenging to synthetic chemists. Alkyl sulfinate reagents have been developed as radical precursors to prepare functionalized heterocycles with the desired alkyl bioisosteres. However, the innate (radical) reactivity of this transformation poses reactivity and regioselectivity challenges for the functionalization of any aromatic or heteroaromatic scaffold. Here we showcase the ability of alkyl sulfinates to engage in sulfurane-mediated C(sp

Identifiers

PMID36864142
PMCPMC10838399
OpenAlexW4322766842

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.