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Record W4385660907 · doi:10.26434/chemrxiv-2023-v6r13

Late-Stage C(sp2)–C(sp3) Diversification via Nickel Oxidative Addition Complexes

2023· preprint· en· W4385660907 on OpenAlexfundno aff
Rubén Martı́n, Carlota Odena, María Lourdes Linares, Nahury Castellanos‐Blanco, Ryan T. McGuire, José Manuel Alonso Segura, A. Dieguez-Vazquez, Eric Tan, Jesús Alcázar, Peter Buijnsters, Santiago Cañellas

Bibliographic record

VenueChemRxiv · 2023
Typepreprint
Languageen
FieldChemistry
TopicCatalytic Cross-Coupling Reactions
Canadian institutionsnot available
FundersAgencia Estatal de InvestigaciónNatural Sciences and Engineering Research Council of CanadaInstitut Català d'Investigació Química
KeywordsNickelGeneralityCombinatorial chemistryOxidative additionCatalysisMoleculeDrug discoveryChemistryComputer scienceMaterials scienceOrganic chemistry

Abstract

fetched live from OpenAlex

Nickel catalysis has emerged as a powerful technique for streamlining the access to exceedingly complex organic molecules from simple precursors. However, nickel-catalyzed cross-couplings with advanced synthetic intermediates still remain a considerable challenge. Herein, we describe a technique based on the utilization of nickel oxidative addition complexes (Ni-OAC) of drug-like molecules as a platform to rapidly and reliably generate lead candidates with enhanced C(sp3) fraction. The potential of Ni-OACs to access new chemical space has been assessed in three different C(sp2)–C(sp3) bond-forming events without recourse to specialized ligand backbones. Reactions with Ni-OACs proceed under exceptionally mild conditions and with improved generality when compared to nickel-catalyzed reactions. The development of an automated process for forging C(sp2)–C(sp3) architectures further illustrates the robustness and generality of Ni-OACs, thus offering a new gateway to expedite the design-make-test-analyze (DMTA) cycle in drug discovery

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 categoriesMeta-epidemiology (narrow), Insufficient payload (model declined to judge)
Consensus categoriesInsufficient payload (model declined to judge)
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 score0.039
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.001
Research integrity0.0010.001
Insufficient payload (model declined to judge)0.0030.002

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 head0.058
GPT teacher head0.303
Teacher spread0.245 · 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 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

Citations3
Published2023
Admission routes1
Has abstractyes

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