Evidence map›Paper›PMID 40828412›Full record

ArticleJournal of the American Chemical Society2025

Migrating Group Strategy for Remote Functionalization of Seven-Membered Rings.

Wenlai Han, Taehwan Hwang, Christina Lian, Simon Kolb, Mina Yamane, Vignesh Palani, Alison E Wendlandt

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.

0numbers the graph read from it
0cells of the map it votes in
5citing 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

5 citing papers in PubMed.

  1. Article
  2. Article
  3. Radical Sampling Enabled Saturated N-Heterocycle Cyclization.Journal of the American Chemical Society · 2026
    Article
  4. Article
  5. 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.

Wenlai HanDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.ORCID 0000-0001-8648-2300
Taehwan HwangDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.ORCID 0000-0002-8396-0255
Christina LianDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
Simon KolbDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.ORCID 0000-0001-6352-4619
Mina YamaneDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.ORCID 0009-0005-8195-9946
Vignesh PalaniDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
Alison E WendlandtDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.ORCID 0000-0003-2970-9817

Funding

Late Stage Stereochemical Editing to Transform the Synthesis of Bioactive MoleculesDP2GM146248 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI WENDLANDT, ALISON · 2021 to 2024
$2.1M
Stereochemical Editing of Quaternary Stereocenters Enabled by Enantioselective Recombination of C–C BondsF32GM153117 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI HWANG, TAEHWAN · 2024 to 2025
$81k
NIGMS NIH HHS DP2 GM146248NIGMS NIH HHS F32 GM153117
6 · The paper itself

Abstract

Seven-membered rings are essential structural components in bioactive compounds, yet their precise synthesis remains challenging compared to smaller ring systems. While traditional approaches rely on ring assembly strategies, direct functionalization of simpler cyclic precursors offers an attractive alternative to substituted building blocks. We report a photocatalytic transannular ketone migration strategy that converts 1,1-disubstituted acylcycloheptanes into 1,4-disubstituted products under mild conditions, promoted by sodium decatungstate and thiol cocatalysts under light-emitting diode (LED) irradiation. The process operates via reversible hydrogen atom abstraction and donation at multiple sites within the ring, followed by site-selective migration via radical addition and β-scission at the exocyclic carbonyl group. This dynamic kinetic approach to site-selective C-H functionalization provides regioselective access to densely substituted seven-membered rings, addressing a longstanding gap in synthetic methodology.

Identifiers

PMID40828412
PMCPMC12536901

What OpenQuestion holds

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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.