Evidence map›Paper›PMID 36044255›Full record

ArticleJournal of the American Chemical Society2022

Copper Hydride-Catalyzed Enantioselective Olefin Hydromethylation.

Yuyang Dong, Kwangmin Shin, Binh Khanh Mai, Peng Liu, Stephen L Buchwald

Open access · greenAbstract read
In one paragraph

Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.

0numbers the graph read from it
0cells of the map it votes in
14citing papers in PubMed
4.8field-weighted citation impact, top 4% 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

14 citing papers in PubMed, 48 citations in OpenAlex.

  1. Catalytic Asymmetric Hydration of Alkenes.Journal of the American Chemical Society · 2026
    Article
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  6. London Dispersion as a Design Element in Molecular Catalysis.Journal of the American Chemical Society · 2025
    Review
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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

5 authors at 2 institutions in 1 country.

Yuyang DongDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.ORCID 0000-0002-4533-4798
Kwangmin ShinDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.ORCID 0000-0002-1708-2351
Binh Khanh MaiDepartment of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.ORCID 0000-0001-8487-1417
Peng LiuDepartment of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.ORCID 0000-0002-8188-632X
Stephen L BuchwaldDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.ORCID 0000-0003-3875-4775
Massachusetts Institute of Technology · USUniversity of Pittsburgh · US

Funding

Metal-Catalyzed Methods for Organic SynthesisR35GM122483 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI STEPHEN L BUCHWALD · 2017 to 2026
$11.4M
LATE TRANSITION METAL CATALYSTS FOR ORGANIC SYNTHESISR01GM058160 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI BUCHWALD, STEPHEN L · 1998 to 2016
$9.0M
Computational Models for Reactivity and Selectivity in Transition Metal-Catalyzed Olefin FunctionalizationR35GM128779 · NIGMS · UNIVERSITY OF PITTSBURGH AT PITTSBURGH · PI Peng Liu · 2018 to 2026
$2.9M
NIGMS NIH HHS R01 GM058160NIGMS NIH HHS R35 GM122483NIGMS NIH HHS R35 GM128779
6 · The paper itself

Abstract

The enantioselective installation of a methyl group onto a small molecule can result in the significant modification of its biological properties. While hydroalkylation of olefins represents an attractive approach to introduce alkyl substituents, asymmetric hydromethylation protocols are often hampered by the incompatibility of highly reactive methylating reagents and a lack of general applicability. Herein, we report an asymmetric olefin hydromethylation protocol enabled by CuH catalysis. This approach leverages methyl tosylate as a methyl source compatible with the reducing base-containing reaction environment, while a catalytic amount of iodide ion transforms the methyl tosylate

Indexed as

AlkenesCopperBenzenesulfonatesCatalysisHydrocarbons, IodinatedStereoisomerismAlkenesBenzenesulfonatesCopperHydrocarbons, Iodinatedmethyl iodidemethyl tosylate

Identifiers

PMID36044255
PMCPMC9994624
OpenAlexW4293802628

What OpenQuestion holds

Textmetadata
LicenceTDM
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.