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Record W2333582106 · doi:10.1021/om201214z

Bis(diethylphosphino)methane As a Bridging Ligand in Complexes of Ir<sub>2</sub>, Rh<sub>2</sub>, and IrRh: Geminal C–H Activation of α-Olefins

2012· article· en· W2333582106 on OpenAlexaff
M.E. Slaney, Dane Anderson, Michael J. Ferguson, Robert McDonald, Martín Cowie

Bibliographic record

VenueOrganometallics · 2012
Typearticle
Languageen
FieldChemistry
TopicCatalytic C–H Functionalization Methods
Canadian institutionsUniversity of Alberta
Fundersnot available
KeywordsChemistryTriflic acidIridiumTrifluoromethanesulfonateHydrideRhodiumProtonationMedicinal chemistryGeminalLigand (biochemistry)MethyleneCatalysisStereochemistryHydrogenOrganic chemistryIon

Abstract

fetched live from OpenAlex

Bis(diethylphosphino)methane (depm, Et 2 PCH 2 PEt 2 ) is used as a new bridging ligand for the syntheses of a series of diiridium, dirhodium, and iridium/rhodium complexes, starting from trans -[MM′Cl 2 (CO) 2 (depm) 2 ] (M = M′ = Ir ( 1 ); M = M′ = Rh ( 11 ); M = Ir, M′ = Rh ( 19 )). The reduction of all three chloro compounds in aqueous KOH under an atmosphere of CO produces the neutral tricarbonyl complexes [MM′(CO) 3 (depm) 2 ] (M = M′ = Ir ( 2 ); M = M′ = Rh ( 12 ); M = Ir, M′ = Rh ( 20 )). Protonation of these tricarbonyl complexes by triflic acid (HOTf) or Brookhart’s acid (HBAr F 4 ) yields the hydride-bridged tricarbonyl complexes [MM′(CO) 3 (μ-H)(depm) 2 ][X] (M = M′ = Ir ( 9 ); M = M′ = Rh ( 16 ); M = Ir, M′ = Rh ( 25 ); X = SO 3 CF 3 or B(3,5-(CF 3 ) 2 C 6 H 3 ) 4 ). Reaction of 2 with methyl triflate yields the methylene/hydride product [Ir 2 (H)(CO) 3 (μ-CH 2 )(depm) 2 ][OTf] ( 4 ), while the same reaction with the dirhodium analogue ( 12 ) produces the methyl complex [Rh 2 (CH 3 )(CO) 3 (depm) 2 ][OTf] ( 14 ) at below −20 °C, which upon warming to above −20 °C results in migratory insertion to yield an acetyl-bridged species, [Rh 2 (CO) 2 (μ-C(CH 3 )O)(depm) 2 ][OTf] ( 14a ). The analogous Rh/Ir species( 20 ) reacts with methyl triflate to give the methyl-tricarbonyl product [IrRh(CH 3 )(CO) 3 (depm) 2 ][OTf] ( 22 ). Removal of a carbonyl from 4 and 22 yields [MIr(CH 3 )(CO) 2 (depm) 2 ][OTf] (M = Ir ( 5 ); M = Rh ( 23 )), which are highly susceptible to hydrolysis; however the dirhodium species 14 and 14a are not susceptible to CO loss under the conditions investigated. The reaction of [Ir 2 (CO) 3 (μ-H)(depm) 2 ][BAr F 4 ] ( 9 ) with a number of α-olefins results in double C–H bond activation of the geminal hydrogens to give the vinylidene-bridged trihydride products of the form [Ir 2 (H) 2 (CO) 2 (μ-H)(μ-C═CRR′)(depm) 2 ][BAr F 4 ].

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)0.001
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow)
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 score0.007
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.001
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0010.000
Bibliometrics0.0000.001
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0000.000

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 head0.021
GPT teacher head0.261
Teacher spread0.240 · 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

Citations24
Published2012
Admission routes1
Has abstractyes

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