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Record W1962774719 · doi:10.1002/047084289x.rn01456

2-(Diphenylphosphino)-2′-(<i>N</i>,<i>N</i>-dimethylamino)-biphenyl

2012· reference-entry· en· W1962774719 on OpenAlexaff
Nicholas Wong, Dirk H. Ortgies, Pat Forgione

Bibliographic record

VenueEncyclopedia of Reagents for Organic Synthesis · 2012
Typereference-entry
Languageen
FieldChemistry
TopicCatalytic Cross-Coupling Reactions
Canadian institutionsConcordia University
Fundersnot available
KeywordsYield (engineering)Ligand (biochemistry)ChemistryBiphenylIodobenzeneMedicinal chemistryAnilinePhosphineDecompositionPhosphine oxideOrganic chemistryCombinatorial chemistryCatalysisMaterials science

Abstract

fetched live from OpenAlex

2-(Diphenylphosphino)-2′-(N,N-dimethylamino)-biphenyl (Ph-Davephos) [240417-00-9] C26H24NP (MW 381.4492) InChI = 1S/C26H24NP/c1-27(2)25-19-11-9-17-23(25)24-18-10-12-20-26(24)28(21-13-5-3-6-14-21)22-15-7-4-8-16-22/h3-20H,1-2H3 InChIKey = JGFXUYLYPITYGR-UHFFFAOYSA-N (phenyl version of Davephos; ligand used for various cross-coupling reactions) Physical Data: mp 124–126 °C.1 Form Supplied in: white powder. Preparation: in 2004, a synthesis of the Ph-Davephos ligand from 2-bromo-iodobenzene was reported in a four-step process with an overall yield of 43%.2 The compound can also be obtained in high yields through the reduction of the corresponding phosphine oxide using DIBAL-H.1 The original Buchwald-type biaryl ligands were prepared using a four-step process starting from 2-bromo-aniline with an overall yield of 29%.3 This synthesis was further optimized to a large scale, one-pot process via the intermediate generation of benzyne.4 Handling, Storage, and Precautions: air sensitive, keep stored under inert gas and in a dry place. Hazardous decomposition products formed under fire conditions.

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)0.001
metaresearch head score (Gemma)0.003
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow), Research integrity, Insufficient payload (model declined to judge)
Consensus categoriesMeta-epidemiology (narrow), Insufficient payload (model declined to judge)
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Not applicable · Consensus signal: Not applicable
GenreCandidate signal: Other · Consensus signal: Other
Teacher disagreement score0.339
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.003
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0020.001
Bibliometrics0.0000.001
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0020.001
Research integrity0.0020.001
Insufficient payload (model declined to judge)0.0310.001

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 head0.018
GPT teacher head0.260
Teacher spread0.242 · 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; both teacher heads agree on what is shown here.

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

Citations0
Published2012
Admission routes1
Has abstractyes

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