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Record W3107060766 · doi:10.1055/s-0040-1705978

Shining Light on the Light-Bearing Element: A Brief Review of Photomediated C–H Phosphorylation Reactions

2020· review· en· W3107060766 on OpenAlexfundno aff
Chao‐Jun Li, Sosthène Ung, Victoria Mechrouk

Bibliographic record

VenueSynthesis · 2020
Typereview
Languageen
FieldChemistry
TopicRadical Photochemical Reactions
Canadian institutionsnot available
FundersFonds Québécois de la Recherche sur la Nature et les TechnologiesNatural Sciences and Engineering Research Council of CanadaCanada Research ChairsMcGill University
KeywordsChemistryRadicalNucleophilePhotoredox catalysisPhotochemistryArylReagentIonic bondingBond cleavageCombinatorial chemistryCatalysisAlkylOrganic chemistryPhotocatalysisIon

Abstract

fetched live from OpenAlex

Abstract Organophosphorus compounds have numerous useful applications, from versatile ligands and nucleophiles in the case of trivalent organophosphorus species to therapeutics, agrochemicals and material additives for pentavalent species. Although phosphorus chemistry is a fairly mature field, the construction of C–P(V) bonds relies heavily on either prefunctionalized substrates such as alkyl or aryl halides, or requires previously oxidized bonds such as C=N or C=O, leading to potential sustainability issues when looking at the overall synthetic route. In light of the recent advances in photochemistry, using photons as a reagent can provide better alternatives for phosphorylations by unlocking radical mechanisms and providing interesting redox pathways. This review will showcase the different photomediated phosphorylation procedures available for converting C–H bonds into C–P(V) bonds. 1 Introduction 1.1 Organophosphorus Compounds 1.2 Phosphorylation: Construction of C–P(V) Bonds 1.3 Photochemistry as an Alternative to Classical Phosphorylations 2 Ionic Mechanisms Involving Nucleophilic Additions 3 Mechanisms Involving Radical Intermediates 3.1 Mechanisms Involving Reactive Carbon Radicals 3.2 Mechanisms Involving Phosphorus Radicals 3.2.1 Photoredox: Direct Creation of Phosphorus Radicals 3.2.2 Photoredox: Indirect Creation of Phosphorus Radicals 3.2.3 Dual Catalysis 3.3 Photolytic Cleavage 4 Conclusion and Outlook

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Not applicable · Consensus signal: none
GenreCandidate signal: Review · Consensus signal: Review
Teacher disagreement score0.003
Threshold uncertainty score0.012

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0010.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0020.002
Science and technology studies0.0000.000
Scholarly communication0.0010.001
Open science0.0000.000
Research integrity0.0010.001
Insufficient payload (model declined to judge)0.0030.002

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.035
GPT teacher head0.295
Teacher spread0.260 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designNot applicable
Domainnot available
GenreReview

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

Quick stats

Citations61
Published2020
Admission routes1
Has abstractyes

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