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Sequential Transformations of Organosulfones on the Basis of Properties of Sulfonyl Groups

2022· article· en· W4220882820 on OpenAlexaff
Masakazu Nambo, Cathleen M. Crudden

Bibliographic record

VenueJournal of Synthetic Organic Chemistry Japan · 2022
Typearticle
Languageen
FieldChemistry
TopicSulfur-Based Synthesis Techniques
Canadian institutionsQueen's University
Fundersnot available
KeywordsSulfonylReagentSubstituentChemistryAlkylationDeprotonationCombinatorial chemistryFunctional groupSurface modificationSulfoneOrganic chemistryCatalysisAlkylPolymer

Abstract

fetched live from OpenAlex

Organosulfone is a chemically-stable and versatile reagent in organic synthesis. The sulfonyl group is a strong electron-withdrawing substituent that permits the rapid functionalization of adjacent positions via deprotonation/alkylation, arylation, or conjugation addition reactions. However, after these reactions, removal of the sulfonyl group using highly reducing reagents is virtually the main choice. Therefore, the development of new methods to introduce various functional groups in the place of sulfonyl group will provide tremendous opportunities for straightforward synthesis of complex molecules. Recently our group has developed several new transformations of sulfone derivatives as reacting templates through α-functionalization followed by carbon-sulfonyl (C-SO2) bond activation. To activate C-SO2 bonds, we have established a new strategy focusing on the development of new catalysis/reagents and the design of sulfonyl groups. These methods could provide facile access to a variety of multiply-arylated structures such as di-, tri-, and tetraarylmethanes from stable and readily available reagents. In addition, the rapid preparation of α-fluorinated arylmethane derivatives by combination with selective α-fluorination of benzyl triflones was achieved, which opens up avenues for the development of unexplored biomolecules. Importantly, this work highlights the unique property of organosulfone to functionalize sp3 carbon centers in a modular manner.

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 score0.004

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
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 integrity0.0000.000
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 head0.018
GPT teacher head0.207
Teacher spread0.189 · 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".

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Citations1
Published2022
Admission routes1
Has abstractyes

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