Evidence map›Paper›PMID 35694363›Full record

ArticleChemical science2022

A practical and sustainable two-component Minisci alkylation

Mohammed Sharique, Jadab Majhi, Roshan K Dhungana, Lisa Marie Kammer, Matthias Krumb, Alexander Lipp, Eugénie Romero, Gary A Molander

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 8 papers.

0numbers the graph read from it
0cells of the map it votes in
8citing 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

8 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. On-DNA hydroalkylation ofChemical science · 2023
    Article
  5. Article
  6. Article
  7. Article
  8. 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

8 authors.

Mohammed ShariqueRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania 231 South 34th Street Philadelphia Pennsylvania 19104-6323 USA gmolandr@sas.upenn.edu.ORCID https://orcid.org/0000-0002-4528-4807
Jadab MajhiRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania 231 South 34th Street Philadelphia Pennsylvania 19104-6323 USA gmolandr@sas.upenn.edu.ORCID https://orcid.org/0000-0001-8600-304X
Roshan K DhunganaRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania 231 South 34th Street Philadelphia Pennsylvania 19104-6323 USA gmolandr@sas.upenn.edu.
Lisa Marie KammerRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania 231 South 34th Street Philadelphia Pennsylvania 19104-6323 USA gmolandr@sas.upenn.edu.ORCID https://orcid.org/0000-0002-5501-7251
Matthias KrumbRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania 231 South 34th Street Philadelphia Pennsylvania 19104-6323 USA gmolandr@sas.upenn.edu.ORCID https://orcid.org/0000-0002-9932-7374
Alexander LippRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania 231 South 34th Street Philadelphia Pennsylvania 19104-6323 USA gmolandr@sas.upenn.edu.
Eugénie RomeroRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania 231 South 34th Street Philadelphia Pennsylvania 19104-6323 USA gmolandr@sas.upenn.edu.
Gary A MolanderRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania 231 South 34th Street Philadelphia Pennsylvania 19104-6323 USA gmolandr@sas.upenn.edu.ORCID https://orcid.org/0000-0002-9114-5584

Funding

Accessing New Chemical Space via Organic SynthesisR35GM131680 · NIGMS · UNIVERSITY OF PENNSYLVANIA · PI MOLANDER, GARY A · 2019 to 2022
$2.4M
Computational Methods for Selective CatalysisR01GM087605 · NIGMS · UNIVERSITY OF PENNSYLVANIA · PI KOZLOWSKI, MARISA C · 2010 to 2019
$2.4M
Targeting Nucleic Acid Junctions with Small MoleculesR01GM118510 · NIGMS · UNIVERSITY OF PENNSYLVANIA · PI CHENOWETH, DAVID MICHAEL · 2016 to 2020
$1.6M
NIGMS NIH HHS R01 GM087605NIGMS NIH HHS R01 GM118510NIGMS NIH HHS R35 GM131680
6 · The paper itself

Abstract

An operationally simple, open-air, and efficient light-mediated Minisci C-H alkylation method is described, based on the formation of an electron donor-acceptor (EDA) complex between nitrogen-containing heterocycles and redox-active esters. In contrast to previously reported protocols, this method does not require a photocatalyst, an external single electron transfer agent, or an oxidant additive. Achieved under mildly acidic and open-air conditions, the reaction incorporates primary-, secondary-, and tertiary radicals, including bicyclo[1.1.1]pentyl (BCP) radicals, along with various heterocycles to generate Minisci alkylation products in moderate to good yields. Additionally, the method is exploited to generate a stereo-enriched, hetereoaryl-substituted carbohydrate.

Identifiers

PMID35694363
PMCPMC9116295

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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.