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Record W4211114445 · doi:10.1002/047084289x.rt049.pub2

Tetrakis(triphenylphosphine)palladium(0)

2017· reference-entry· en· W4211114445 on OpenAlexaff
Richard W. Friesen, Emmanuelle M. D. Allouche

Bibliographic record

VenueEncyclopedia of Reagents for Organic Synthesis · 2017
Typereference-entry
Languageen
FieldChemistry
TopicCatalytic Cross-Coupling Reactions
Canadian institutionsUniversité de MontréalMerck Canada Inc. (Canada)
Fundersnot available
KeywordsChemistryPalladiumTriphenylphosphineHydrazine (antidepressant)ReagentInert gasElectrophileReactivity (psychology)ChloroformSolubilityHydrolysisCarbon fibersCatalysisOrganic chemistryMedicinal chemistryMaterials scienceChromatography

Abstract

fetched live from OpenAlex

[14221-01-3] C72H60P4Pd (MW 1155.62) InChI = 1S/4C18H15P.Pd/c4*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;/h4*1-15H; InChIKey = NFHFRUOZVGFOOS-UHFFFAOYSA-N (catalyzes carbon–carbon bond formation of organometallics with a wide variety of electrophiles;2 in combination with other reagents, catalyzes the reduction of a variety of functional groups;3 catalyzes carbon–metal (Sn, Si) bond formation;4 catalyzes deprotection of the allyloxycarbonyl group5) Physical Data: mp has been reported to vary between 100–116 °C (dec) and is not a good indication of purity. Solubility: insol saturated hydrocarbons; moderately sol many other organic solvents including CHCl3, DME, THF, DMF, PhMe, benzene. Form Supplied in: yellow, crystalline solid from various sources. The quality of batches from the same source have been noted to be highly variable and can dramatically alter the expected reactivity. Preparative Methods: readily prepared by the reduction of PdCl2(Ph3P)26 with Hydrazine or by the reaction of Tris(dibenzylideneacetone)dipalladium–Chloroform with Triphenylphosphine.7 Handling, Storage, and Precautions: is air and light sensitive and should be stored in an inert atmosphere in the absence of light. It can be handled for short periods quickly in the air but best results are achieved by handling in a glove box or glove bag under argon or nitrogen.

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 distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.007
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow), Research integrity, Insufficient payload (model declined to judge)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Not applicable · Consensus signal: Not applicable
GenreCandidate signal: Other · Consensus signal: Other
Teacher disagreement score0.234
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.007
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0020.001
Bibliometrics0.0000.000
Science and technology studies0.0010.000
Scholarly communication0.0000.000
Open science0.0020.000
Research integrity0.0010.001
Insufficient payload (model declined to judge)0.0140.000

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 head0.020
GPT teacher head0.277
Teacher spread0.257 · 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 teacher head, not a consensus.

Study designNot applicable
Domainnot available
GenreOther

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

Citations3
Published2017
Admission routes1
Has abstractyes

Explore more

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