Evidence map›Paper›PMID 37727697›Full record

ArticleACS catalysis2022

Kinetic and Thermodynamic Considerations in the Rh-Catalyzed Enantioselective Hydrogenation of 2-Pyridyl-Substituted Alkenes.

Wei Hao, Candice L Joe, Andrea Darù, Sloan Ayers, Antonio Ramirez, Bhupinder Sandhu, Ryan A Daley, Jason S Chen, Michael A Schmidt, Donna G Blackmond

Abstract read
In one paragraph

Article in ACS catalysis, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing 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

2 citing papers in PubMed.

  1. Article
  2. Review
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

10 authors.

Wei HaoDepartment of Chemistry, Scripps Research, La Jolla, California 92037, United States.ORCID 0000-0001-9493-6894
Candice L JoeChemical Process Development, Bristol Myers Squibb Co., New Brunswick, New Jersey 08903, United States.ORCID 0000-0002-7167-2416
Andrea DarùDepartment of Chemistry, Scripps Research, La Jolla, California 92037, United States.ORCID 0000-0002-0825-2101
Sloan AyersChemical Process Development, Bristol Myers Squibb Co., New Brunswick, New Jersey 08903, United States.ORCID 0000-0003-3562-1846
Antonio RamirezChemical Process Development, Bristol Myers Squibb Co., New Brunswick, New Jersey 08903, United States.ORCID 0000-0003-2636-6855
Bhupinder SandhuChemical Process Development, Bristol Myers Squibb Co., New Brunswick, New Jersey 08903, United States.
Ryan A DaleyDepartment of Chemistry, Scripps Research, La Jolla, California 92037, United States.
Jason S ChenDepartment of Chemistry and Automated Synthesis Facility, Scripps Research, La Jolla, California 92037, United States.
Michael A SchmidtChemical Process Development, Bristol Myers Squibb Co., New Brunswick, New Jersey 08903, United States.ORCID 0000-0002-4880-2083
Donna G BlackmondDepartment of Chemistry, Scripps Research, La Jolla, California 92037, United States.ORCID 0000-0001-9829-8375

Funding

Parallel Pressure Reactor with Sampling CapabilitiesS10OD025208 · OD · SCRIPPS RESEARCH INSTITUTE, THE · PI CHEN, JASON SHIH-HAO · 2018 to 2018
$591k
NIH HHS S10 OD025208
6 · The paper itself

Abstract

The mechanism of asymmetric hydrogenation of 2-pyridyl alkenes catalyzed by chiral Rh-phosphine complexes at ambient temperature is examined using kinetic, spectroscopic, and computational tools. The reaction proceeds with reversible substrate binding followed by rate-determining addition of hydrogen. Substrate binding occurs only through the pyridine nitrogen in contrast to other substrate classes exhibiting stronger substrate direction. The lack of influence of hydrogen pressure on the product enantiomeric excess suggests that a pre-equilibrium in substrate binding is maintained across the pressure range investigated. An off-cycle Rh-hydride species is implicated in the mild catalyst deactivation observed. In contrast to Ru-phosphine-catalyzed reactions of the same substrate class, the stereochemical outcome in this system correlates generally with the relative stability of the

Indexed as

asymmetric hydrogenationkineticsreaction progress kinetic analysistransition metal catalysistrisubstituted olefins

Identifiers

PMID37727697
PMCPMC10508913

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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.