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Record W2766664475 · doi:10.1002/anie.201707958

Visible‐Light‐Initiated Manganese Catalysis for C−H Alkylation of Heteroarenes: Applications and Mechanistic Studies

2017· article· en· W2766664475 on OpenAlexafffund
Philippe Nuhant, Martins S. Oderinde, Julien Genovino, Antoine Juneau, Yohann Gagné, Christophe Allais, Gary M. Chinigo, Chulho Choi, Neal W. Sach, Louise Bernier, Yvette M. Fobian, Mark W. Bundesmann, Bhagyashree Khunte, Mathieu Frenette, Olugbeminiyi Fadeyi

Bibliographic record

VenueAngewandte Chemie International Edition · 2017
Typearticle
Languageen
FieldChemistry
TopicRadical Photochemical Reactions
Canadian institutionsUniversité du Québec à Montréal
FundersNatural Sciences and Engineering Research Council of CanadaPfizer
KeywordsManganeseAlkylationCatalysisChemistryVisible spectrumCombinatorial chemistryPhotochemistryOrganic chemistryMaterials scienceOptoelectronics

Abstract

fetched live from OpenAlex

Abstract A visible‐light‐driven Minisci protocol that employs an inexpensive earth‐abundant metal catalyst, decacarbonyldimanganese Mn2(CO)10, to generate alkyl radicals from alkyl iodides has been developed. This Minisci protocol is compatible with a wide array of sensitive functional groups, including oxetanes, sugar moieties, azetidines, tert‐butyl carbamates (Boc‐group), cyclobutanes, and spirocycles. The robustness of this protocol is demonstrated on the late‐stage functionalization of complex nitrogen‐containing drugs. Photophysical and DFT studies indicate a light‐initiated chain reaction mechanism propagated by .Mn(CO)5. The rate‐limiting step is the iodine abstraction from an alkyl iodide by .Mn(CO)5.

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)0.000
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
Metaresearch0.0000.000
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)0.0010.000

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 head0.343
Teacher spread0.295 · 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

Citations186
Published2017
Admission routes2
Has abstractyes

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