Evidence map›Paper›PMID 35774162›Full record

ArticleChemical science2022

Hydroxy-directed fluorination of remote unactivated C(sp

Stefan Andrew Harry, Michael Richard Xiang, Eric Holt, Andrea Zhu, Fereshte Ghorbani, Dhaval Patel, Thomas Lectka

Abstract read
In one paragraph

Article in Chemical science, 2022. 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
–field-weighted citation impact
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.

  1. Article
  2. Review
  3. 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.

Stefan Andrew HarryDepartment of Chemistry, Johns Hopkins University 3400 N. Charles St. Baltimore MD 21218 USA lectka@jhu.edu.ORCID https://orcid.org/0000-0002-5479-4008
Michael Richard XiangDepartment of Chemistry, Johns Hopkins University 3400 N. Charles St. Baltimore MD 21218 USA lectka@jhu.edu.
Eric HoltDepartment of Chemistry, Johns Hopkins University 3400 N. Charles St. Baltimore MD 21218 USA lectka@jhu.edu.
Andrea ZhuDepartment of Chemistry, Johns Hopkins University 3400 N. Charles St. Baltimore MD 21218 USA lectka@jhu.edu.
Fereshte GhorbaniDepartment of Chemistry, Johns Hopkins University 3400 N. Charles St. Baltimore MD 21218 USA lectka@jhu.edu.
Dhaval PatelDepartment of Chemistry, Johns Hopkins University 3400 N. Charles St. Baltimore MD 21218 USA lectka@jhu.edu.
Thomas LectkaDepartment of Chemistry, Johns Hopkins University 3400 N. Charles St. Baltimore MD 21218 USA lectka@jhu.edu.

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

We report a photochemically induced, hydroxy-directed fluorination that addresses the prevailing challenge of high diastereoselectivity in this burgeoning field. Numerous simple and complex motifs showcase a spectrum of regio- and stereochemical outcomes based on the configuration of the hydroxy group. Notable examples include a long-sought switch in the selectivity of the refractory sclareolide core, an override of benzylic fluorination, and a rare case of 3,3'-difluorination. Furthermore, calculations illuminate a low barrier transition state for fluorination, supporting our notion that alcohols are engaged in coordinated reagent direction. A hydrogen bonding interaction between the innate hydroxy directing group and fluorine is also highlighted for several substrates with

Identifiers

PMID35774162
PMCPMC9200124

What OpenQuestion holds

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LicenceCC BY
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Registered trials

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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.