Evidence map›Paper›PMID 38723265›Full record

ArticleJournal of the American Chemical Society2024

CuH-Catalyzed Regio- and Enantioselective Formal Hydroformylation of Vinyl Arenes.

Subhash Garhwal, Yuyang Dong, Binh Khanh Mai, Peng Liu, Stephen L Buchwald

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.

0numbers the graph read from it
0cells of the map it votes in
4citing 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

4 citing papers in PubMed.

  1. Article
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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.

Subhash GarhwalDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.ORCID 0000-0002-0093-9224
Yuyang DongDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.ORCID 0000-0002-4533-4798
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

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

A highly enantioselective formal hydroformylation of vinyl arenes enabled by copper hydride (CuH) catalysis is reported. Key to the success of the method was the use of the mild Lewis acid zinc triflate to promote the formation of oxocarbenium electrophiles through the activation of diethoxymethyl acetate. Using the newly developed protocol, a broad range of vinyl arene substrates underwent efficient hydroacetalization reactions to provide access to highly enantioenriched α-aryl acetal products in good yields with exclusively branched regioselectivity. The acetal products could be converted to the corresponding aldehydes, alcohols, and amines with full preservation of the enantiomeric purity. Density functional theory studies support that the key C-C bond-forming event between the alkyl copper intermediate and the oxocarbenium electrophile takes place with inversion of configuration of the Cu-C bond in a backside S

Identifiers

PMID38723265
PMCPMC11439487

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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.