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Record W4283771971 · doi:10.1021/acsomega.2c01092

Phenylboronic Ester-Activated Aryl Iodide-Selective Buchwald–Hartwig-Type Amination toward Bioactivity Assay

2022· article· en· W4283771971 on OpenAlexaff
Raghu Nath Dhital, Abhijit Sen, Hao Hu, Rikako Ishii, Takuma Sato, Yoko Yashiroda, Hiromi Kimura, Charles Boone, Minoru Yoshida, Yushi Futamura, Hiroyuki Hirano, Hiroyuki Osada, Daisuke Hashizume, Yasuhiro Uozumi, Yoichi M. A. Yamada

Bibliographic record

VenueACS Omega · 2022
Typearticle
Languageen
FieldChemistry
TopicCatalytic Cross-Coupling Reactions
Canadian institutionsUniversity of Toronto
FundersCreations of Advanced Catalytic Transformation for the Sustainable Manufacturing at Low Energy, Low Environmental LoadJapan Society for the Promotion of ScienceFugaku Trust for Medicinal ResearchAccelerated Innovation Research Initiative Turning Top Science and Ideas into High-Impact ValuesTakeda Science FoundationRIKENJapan Agency for Medical Research and DevelopmentNaito Foundation
KeywordsArylPhenylboronic acidChemistryAminationIodideOrganic chemistryMedicinal chemistryCombinatorial chemistryCatalysis

Abstract

fetched live from OpenAlex

High Resolution Image Download MS PowerPoint Slide In this study, a phenylboronic ester-activated aryl iodide-selective Buchwald–Hartwig-type amination was developed. When the reaction of aryl iodides and aryl/aliphatic amines using Ni(acac) 2 is carried out in the presence of phenylboronic ester, the Buchwald–Hartwig-type amination proceeds smoothly to afford the corresponding amines in high yields. This reaction does not proceed in the absence of phenylboronic ester. A wide variety of aryl iodides can be applied in the presence of aryl chlorides and bromides, which remain intact during the reaction. The mechanistic studies of this reaction suggest that the phenylboronic ester acts as an activator for the amines to form the ″ate complex″. Chemical kinetics studies show that the reaction of aryl iodides, base, and Ni(acac) 2 follows first-order kinetics, while that of amines and phenylboronic ester follows zero-order kinetics. The bioactivity screening of the corresponding products showed that some amination products exhibit antifungal activity.

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 machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.001
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation 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 score0.001
Threshold uncertainty score0.003

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0010.000
Meta-epidemiology (narrow)0.0010.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0010.001
Insufficient payload (model declined to judge)0.0010.001

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 head0.022
GPT teacher head0.271
Teacher spread0.250 · 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 source (direct Gemma or distilled Codex), 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

Citations3
Published2022
Admission routes1
Has abstractyes

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