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Record W2328387874 · doi:10.1021/om200784j

Regioselective C–H Activation of Cyclometalated Bis-Tridentate Ruthenium Complexes

2011· article· en· W2328387874 on OpenAlexafffund
Stacy S. R. Muise, Holly A. Severin, Bryan D. Koivisto, Kiyoshi C. D. Robson, Eduardo Schott, Curtis P. Berlinguette

Bibliographic record

VenueOrganometallics · 2011
Typearticle
Languageen
FieldChemistry
TopicCatalytic C–H Functionalization Methods
Canadian institutionsUniversity of Calgary
FundersNatural Sciences and Engineering Research Council of Canada
KeywordsChemistryRegioselectivityAgostic interactionMetathesisElectrophileSubstituentRing (chemistry)Steric effectsMetalationRutheniumMedicinal chemistryStereochemistryBorylationMoietySalt metathesis reactionMetalArylCatalysisOrganic chemistryAlkylPolymerization

Abstract

fetched live from OpenAlex

A series of bis - tridentate Ru(II) complexes consisting of trimethyl-4,4′,4″-tricarboxylate-2,2′:6′,2″-terpyridine (Me 3 tctpy) and derivatized 6-phenyl-2,2′-bipyridine (pbpy) ligands are reported. Each complex is attached to a terminal triphenylamine (TPA) substituent at the central ring of pbpy through a thiophene bridge to benefit light absorption, while the anionic ring of pbpy is functionalized with substituents to modulate the metal-based redox potential. The cyclometalation step was found to favor the isomer where the electron-donating groups (EDGs; i.e., −OEt, −SEt) are situated ortho to the organometallic bond rather than the sterically favored para position, while the para isomer is formed in exclusivity when electron-withdrawing groups (e.g., −CF 3 ) are installed on the anionic ring. Moreover, the distribution of the isomeric products is affected by the identity of the chalcogen: ortho: para = 1:0 and 3:1 where EDG = −OEt and −SEt, respectively. Because our molecular scaffold rules out certain cyclometalation pathways (e.g., oxidative addition, agostic interactions, σ-bond metathesis), we are able to experimentally establish that the observed regioselectivity is in accordance with an electrophilic metalation where the relative stabilities of the products and carbanionic intermediates govern the ratio of the isomers formed.

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 score0.060
Threshold uncertainty score0.987

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
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)0.0140.000

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 head0.048
GPT teacher head0.270
Teacher spread0.222 · 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

Citations10
Published2011
Admission routes2
Has abstractyes

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