Evidence map›Paper›PMID 34387898›Full record

ArticleChemistry (Weinheim an der Bergstrasse, Germany)2021

Continuous Flow Acylation of (Hetero)aryllithiums with Polyfunctional N,N-Dimethylamides and Tetramethylurea in Toluene.

Dimitrije Djukanovic, Benjamin Heinz, Francesca Mandrelli, Serena Mostarda, Paolo Filipponi, Benjamin Martin, Paul Knochel

Open access · hybridAbstract read
In one paragraph

Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2021. 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
1.3field-weighted citation impact, top 22% 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

5 citing papers in PubMed, 14 citations in OpenAlex.

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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 2 institutions in 2 countries.

Dimitrije DjukanovicDepartment Chemie, Ludwig-Maximilians-Universität München, Butenandtstraße 5-13, Haus F, 81377, Munich, Germany.
Benjamin HeinzDepartment Chemie, Ludwig-Maximilians-Universität München, Butenandtstraße 5-13, Haus F, 81377, Munich, Germany.
Francesca MandrelliNovartis Pharma AG, Chemical Development Fabrikstraße, 4002, Basel, Switzerland.
Serena MostardaNovartis Pharma AG, Chemical Development Fabrikstraße, 4002, Basel, Switzerland.
Paolo FilipponiNovartis Pharma AG, Chemical Development Fabrikstraße, 4002, Basel, Switzerland.
Benjamin MartinNovartis Pharma AG, Chemical Development Fabrikstraße, 4002, Basel, Switzerland.
Paul KnochelDepartment Chemie, Ludwig-Maximilians-Universität München, Butenandtstraße 5-13, Haus F, 81377, Munich, Germany.
Novartis (Switzerland) · CHLudwig-Maximilians-Universität München · DE

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

The continuous flow reaction of various aryl or heteroaryl bromides in toluene in the presence of THF (1.0 equiv) with sec-BuLi (1.1 equiv) provided at 25 °C within 40 sec the corresponding aryllithiums which were acylated with various functionalized N,N-dimethylamides including easily enolizable amides at -20 °C within 27 sec, producing highly functionalized ketones in 48-90 % yield (36 examples). This method was well suited for the preparation of α-chiral ketones such as naproxene and ibuprofen derived ketones with 99 % ee. A one-pot stepwise bis-addition of two different lithium organometallics to 1,1,3,3-tetramethyurea (TMU) provided unsymmetrical ketones in 69-79 % yield (9 examples).

Indexed as

TolueneMethylurea Compounds1,1,3,3-tetramethylureaMethylurea CompoundsTolueneacylationamidecontinuous flowlithiumtoluene

Identifiers

PMID34387898
PMCPMC8519161
OpenAlexW3190734660

What OpenQuestion holds

Textmetadata
LicenceCC BY
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.