Evidence map›Paper›PMID 28671461›Full record

ArticleThe Journal of organic chemistry2017

Mechanistic Studies of Formal Thioboration Reactions of Alkynes.

Adena Issaian, Darius J Faizi, Johnathan O Bailey, Peter Mayer, Guillaume Berionni, Daniel A Singleton, Suzanne A Blum

Open access · greenAbstract read
In one paragraph

Article in The Journal of organic chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing papers in PubMed
1.8field-weighted citation impact, top 16% 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

2 citing papers in PubMed, 24 citations in OpenAlex.

  1. Metal-Free Electrophilic Borylative Cyclizations of Alkynes.Chemical record (New York, N.Y.) · 2026
    Review
  2. 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

7 authors at 3 institutions in 2 countries.

Adena IssaianDepartment of Chemistry, University of California , Irvine, California 92617-2025, United States.
Darius J FaiziDepartment of Chemistry, University of California , Irvine, California 92617-2025, United States.
Johnathan O BaileyDepartment of Chemistry, Texas A&M University , P.O. Box 30012, College Station, Texas 77842, United States.
Peter MayerDepartment of Chemistry, Ludwig Maximilian University of Munich , Munich, 80539, Germany.
Guillaume BerionniDepartment of Chemistry, Ludwig Maximilian University of Munich , Munich, 80539, Germany.ORCID 0000-0002-5422-9113
Daniel A SingletonDepartment of Chemistry, Texas A&M University , P.O. Box 30012, College Station, Texas 77842, United States.ORCID 0000-0003-3656-1339
Suzanne A BlumDepartment of Chemistry, University of California , Irvine, California 92617-2025, United States.ORCID 0000-0002-8055-1405
University of California, Irvine · USLudwig-Maximilians-Universität München · DETexas A&M University · US

Funding

New Concepts In Organic Selectivity and MechanismsR01GM045617 · NIGMS · TEXAS A&M UNIVERSITY SYSTEM · PI SINGLETON, DANIEL A · 1991 to 2019
$4.5M
Bond-Forming Methods via Dual-Metal Catalysis with Organogold IntermediatesR01GM098512 · NIGMS · UNIVERSITY OF CALIFORNIA-IRVINE · PI BLUM, SUZANNE A. · 2012 to 2015
$1.1M
NIGMS NIH HHS R01 GM045617NIGMS NIH HHS R01 GM098512
6 · The paper itself

Abstract

Several formal heteroborylative cyclization reactions have been recently reported, but little physical-organic and mechanistic data are known. We now investigate the catalyst-free formal thioboration reaction of alkynes to gain mechanistic insight into B-chlorocatecholborane (ClBcat) in its new role as an alkynophilic Lewis acid in electrophilic cyclization/dealkylation reactions. In kinetic studies, the reaction is second-order globally and first-order with respect to both the 2-alkynylthioanisole substrate and the ClBcat electrophile, with activation parameters of ΔG

Indexed as

AlkynesBoratesCyclizationKineticsModels, MolecularMolecular StructureQuantum TheorySulfhydryl CompoundsThermodynamicsAlkynesBoratesSulfhydryl Compounds

Identifiers

PMID28671461
PMCPMC5826600
OpenAlexW2725503889

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.