MétaCan
Menu
Back to cohort
Record W2086573134 · doi:10.1021/om020241a

Stoichiometric and Catalytic Oxidation of BINAP by Dioxygen in a Rhodium(I) Complex

2002· article· en· W2086573134 on OpenAlexaff
Kevin A. Bunten, David H. Farrar, Anthony J. Poë, Alan J. Lough

Bibliographic record

VenueOrganometallics · 2002
Typearticle
Languageen
FieldChemistry
TopicAsymmetric Hydrogenation and Catalysis
Canadian institutionsUniversity of Toronto
Fundersnot available
KeywordsBINAPChemistryLigand (biochemistry)RhodiumCatalysisAdductStoichiometryOxygenMedicinal chemistryPhotochemistryInorganic chemistryOrganic chemistryEnantioselective synthesis

Abstract

fetched live from OpenAlex

The square planar complex (BINAP)Rh(CO)Cl (BINAP = 2,2‘-bis(diphenylphosphino)-1,1‘-binaphthyl) was synthesized from [Rh(COD)Cl] 2 (COD = 1,5 cyclooctadiene) and BINAP under a CO atmosphere. It reacts with oxygen to form the square planar (BINAP(O))Rh(CO)Cl in approximately 50% yield, along with molar equivalents of free BINAP dioxide (BINAP(O) 2 ) and CO 2 . The oxygen atom of the BINAP(O) was shown crystallographically to be trans to the CO ligand. In the presence of excess BINAP under CO/O 2 gas mixtures, the reaction is catalytic with a TOF of 0.16 h - 1 at ambient temperature in chloroform. The kinetics of this transformation were investigated and conditions for optimum selectivity for BINAP(O) formation suggested. A stoichiometric mechanism is proposed that involves initial formation of an O 2 adduct, followed by oxygen atom transfer to both phosphorus atoms of BINAP or to one phosphorus atom and the CO ligand trans to it. These processes might be concerted, or stepwise with intermediate Rh O species. To the best of our knowledge, this chemistry represents the first example of a reaction exhibiting oxygen atom addition from O 2 either to both phosphorus atoms in a bisphosphine ligand or to one phosphorus atom and a CO ligand in the same complex.

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)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesInsufficient payload (model declined to judge)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.105
Threshold uncertainty score0.998

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0010.003
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0030.000

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 head0.211
Teacher spread0.191 · 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 designBench or experimental
Domainnot available
GenreEmpirical

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

Citations51
Published2002
Admission routes1
Has abstractyes

Explore more

Same venueOrganometallicsSame topicAsymmetric Hydrogenation and CatalysisFrench-language works237,207