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Record W2022671001 · doi:10.1021/ic060127a

Rh(I) and Ir(I) Derivatives of a P(S),N-Substituted Indene Ligand:  Synthetic, Structural, and Catalytic Alkene Hydrosilylation Studies

2006· article· en· W2022671001 on OpenAlexaff
Dominik Wechsler, Anne L. Myers, Robert McDonald, Michael J. Ferguson, Mark Stradiotto

Bibliographic record

VenueInorganic Chemistry · 2006
Typearticle
Languageen
FieldChemistry
TopicAsymmetric Hydrogenation and Catalysis
Canadian institutionsUniversity of AlbertaDalhousie University
Fundersnot available
KeywordsIndeneChemistryMedicinal chemistryTriethylsilaneAlkeneCatalysisHydrosilylationCyclooctadieneHydroaminationDenticityLigand (biochemistry)StereochemistryOrganic chemistryMetal

Abstract

fetched live from OpenAlex

Treatment of 1-PiPr2-indene or 1-PiPr2-2-NMe2-indene (1a) with elemental sulfur afforded 3-iPr2P(S)-indene or 1-iPr2P(S)-2-NMe2-indene (4a) in 81% and 85% isolated yield, respectively. Addition of 4a to [(COD)M(THF)2]+BF4- afforded the corresponding [(COD)M(kappa2-N,S-4a)]+BF4- complexes (M = Rh, 5a, 76%; M = Ir, 5b, 59%; COD = eta4-1,5-cyclooctadiene), which were found to exhibit temperature-dependent NMR spectral features that were rationalized in terms of a dynamic process involving M-NMe2 dissociation, rotation about the indenyl-NMe2 bond, inversion at nitrogen, and re-coordination to M. Analysis of variable-temperature NMR data collected for 5a and 5b each yielded a value for DeltaG(double dagger) of ca. 14 kcal/mol for this process. Exposure of 5a or 5b to NaN(SiMe3)2 generated the corresponding (COD)M(kappa2-C,S-1-iPr2P(S)-2-NMe2-(C1-indenyl)) complex (M = Rh, 6a, 70%; M = Ir, 6b, 86%) in which the metal is incorporated into an M-C-P-S ring via coordination to the indenyl ring in an eta1-fashion, as well as to sulfur. Alternatively, complex 6b was prepared cleanly via lithiation of 4a followed by treatment with 0.5 equiv of [(COD)IrCl]2. The ability of 5a,b and 6a,b to mediate the addition of triethylsilane to styrene was also explored, and their performance was compared with that of Wilkinson's Catalyst ((PPh3)3RhCl) and Crabtree's catalyst ([(COD)Ir(PCy3)(Py)]+PF6-; Cy = cyclohexyl; Py = pyridine). Single-crystal X-ray diffraction data are provided for 4a, 2-NMe2-3-iPr2P(S)-indene (4b), 6a, and 6b.

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 categoriesnone
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 score0.006
Threshold uncertainty score0.924

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
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 head0.009
GPT teacher head0.232
Teacher spread0.223 · 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.

The models applied no category: nothing in the taxonomy fit this work.
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

Citations23
Published2006
Admission routes1
Has abstractyes

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