Evidence map›Paper›PMID 36503915›Full record

ArticleChemical communications (Cambridge, England)2023

Facile synthesis of sulfonyl fluorides from sulfonic acids.

Brodie J Thomson, Samuel R Khasnavis, Emma C Grigorian, Rohun Krishnan, Theodore D Yassa, Kelvin Lee, Glenn M Sammis, Nicholas D Ball

Open access · hybridAbstract read
In one paragraph

Article in Chemical communications (Cambridge, England), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.

0numbers the graph read from it
0cells of the map it votes in
3citing papers in PubMed
2.8field-weighted citation impact, top 9% 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

3 citing papers in PubMed, 27 citations in OpenAlex.

  1. Article
  2. Article
  3. Review
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 2 institutions in 2 countries.

Brodie J ThomsonDepartment of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia V6T 1Z1, Canada. gsammis@chem.ubc.ca.
Samuel R KhasnavisDepartment of Chemistry, Pomona College, 645 North College Avenue, Claremont, California 91711, USA. nicholas.ball@pomona.edu.
Emma C GrigorianDepartment of Chemistry, Pomona College, 645 North College Avenue, Claremont, California 91711, USA. nicholas.ball@pomona.edu.
Rohun KrishnanDepartment of Chemistry, Pomona College, 645 North College Avenue, Claremont, California 91711, USA. nicholas.ball@pomona.edu.
Theodore D YassaDepartment of Chemistry, Pomona College, 645 North College Avenue, Claremont, California 91711, USA. nicholas.ball@pomona.edu.
Kelvin LeeDepartment of Chemistry, Pomona College, 645 North College Avenue, Claremont, California 91711, USA. nicholas.ball@pomona.edu.
Glenn M SammisDepartment of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia V6T 1Z1, Canada. gsammis@chem.ubc.ca.ORCID http://orcid.org/0000-0002-8204-8571
Nicholas D BallDepartment of Chemistry, Pomona College, 645 North College Avenue, Claremont, California 91711, USA. nicholas.ball@pomona.edu.ORCID http://orcid.org/0000-0002-6816-1113
Pomona College · USUniversity of British Columbia · CA

Funding

Sulfur-Fluoride Exchange (SuFEx) Reactions toward Nitrogen-Based Sulfur(VI) CompoundsR15GM134457 · NIGMS · POMONA COLLEGE · PI BALL, NICHOLAS D · 2020 to 2025
$822k
NIGMS NIH HHS R15 GM134457
6 · The paper itself

Abstract

Herein, we demonstrate two complementary strategies for the syntheses of sulfonyl fluorides using sulfonic acids and their salts. One strategy involves the conversion of sulfonic acid sodium salts to sulfonyl fluorides using thionyl fluoride in 90-99% yields in one hour. Lessons learned from the mechanism of this reaction also have enabled a complementary deoxyfluorination of sulfonic acids using Xtalfluor-E® - a bench stable solid - allowing for the conversion of both aryl and alkyl sulfonic acids and salts to sulfonyl fluorides in 41-94% yields. Notably, using Xtalfluor-E® enabled milder conditions and the use of both sulfonic acids and their sodium salts.

Indexed as

FluoridesSulfonic AcidsHydrocarbons, FluorinatedSaltsSodiumSulfinic AcidsSulfur Compoundsdiethylaminodifluorosulfinium tetrafluoroborateFluoridesHydrocarbons, FluorinatedSaltsSodiumSulfinic AcidsSulfonic AcidsSulfur Compoundssulfuryl fluoride

Identifiers

PMID36503915
PMCPMC9835472
OpenAlexW4311203986

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.