Evidence map›Paper›PMID 39899756›Full record

ArticleChemistry (Weinheim an der Bergstrasse, Germany)2025

Development of a Highly Selective Synthesis of 4-Substituted Tetrahydroquinolines: Substrate Scope and Mechanistic Study.

Jeanette Piña, Lupita S Aguirre, Levi T Litwiller, Hai T Ly, Michael P Crockett, Andy A Thomas

Abstract read
In one paragraph

Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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

0 citing papers in PubMed.

No citing paper in PubMed yet.

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

6 authors.

Jeanette PiñaDepartment of Chemistry, Texas A&M University, 580 Ross St, College Station, TX, USA, 77843 1.ORCID https://orcid.org/0000-0003-3970-9263
Lupita S AguirreDepartment of Chemistry, Texas A&M University, 580 Ross St, College Station, TX, USA, 77843 1.ORCID https://orcid.org/0000-0001-8754-1608
Levi T LitwillerDepartment of Chemistry, Texas A&M University, 580 Ross St, College Station, TX, USA, 77843 1.ORCID https://orcid.org/0000-0002-1679-1500
Hai T LyDepartment of Chemistry, Texas A&M University, 580 Ross St, College Station, TX, USA, 77843 1.ORCID https://orcid.org/0009-0004-2629-6812
Michael P CrockettDepartment of Chemistry, Texas A&M University, 580 Ross St, College Station, TX, USA, 77843 1.ORCID https://orcid.org/0000-0002-6165-2841
Andy A ThomasDepartment of Chemistry, Texas A&M University, 580 Ross St, College Station, TX, USA, 77843 1.ORCID https://orcid.org/0000-0001-6336-5566

Funding

Lewis Base Ligands Designed to Control Carbon-Carbon Bond FormationR35GM151018 · NIGMS · TEXAS A&M UNIVERSITY · PI Andy Alexander Thomas · 2023 to 2026
$1.5M
NIGMS NIH HHS R35 GM151018Welch Foundation A-2081-20240404
6 · The paper itself

Abstract

Herein, we describe a general and selective deprotonation functionalization reaction of tetrahydroquinolines at the 4-position using organolithiums and phosphoramide ligands. In addition to the development of a direct deprotonation alkylation reaction with primary and secondary alkyl halides, a Negishi cross-coupling protocol was realized to afford products with a range of aromatic halides. These methods were applied to the late-stage installation of tetrahydroquinolines into a variety of substrates including pharmaceuticals as well as natural product analogues. The use of thorough mechanistic investigations revealed the aggregation state of the newly formed tetrahydroquinoline anion to be a separated ion pair, which proved critical to optimizing the reaction conditions.

Indexed as

direct alkylationNegishi cross-couplingsorganozincseparated ion pairstetrahydroquinoline

Identifiers

PMID39899756
PMCPMC13038347

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.