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Record W3194452403 · doi:10.1002/cmtd.202100053

Rapid and Mild One‐Flow Synthetic Approach to Unsymmetrical Sulfamides Guided by Bayesian Optimization

2021· article· en· W3194452403 on OpenAlexaff
Naoto Sugisawa, Hiroki Sugisawa, Yuma Otake, Roman V. Krems, Hiroyuki Nakamura, Shinichiro Fuse

Bibliographic record

VenueChemistry - Methods · 2021
Typearticle
Languageen
FieldEngineering
TopicInnovative Microfluidic and Catalytic Techniques Innovation
Canadian institutionsUniversity of British Columbia
Fundersnot available
KeywordsSulfuryl chlorideBayesian optimizationYield (engineering)ChemistryCombinatorial chemistryReaction conditionsBiochemical engineeringMaterials scienceOrganic chemistryMathematicsMathematical optimizationCatalysisEngineering

Abstract

fetched live from OpenAlex

Abstract Bayesian optimization (BO) is regarded as an efficient approach that can identify optimal conditions using a restricted number of experiments. Despite demonstrated potential of BO, applications of BO‐based approaches in synthetic organic chemistry remain limited. Herein, we achieved the first rapid and mild (5.1 s, 20 °C) one‐flow synthesis of unsymmetrical sulfamides from inexpensive sulfuryl chloride. Undesired reactions were successfully suppressed and the risk in handling sulfuryl chloride was minimized by the use of micro‐flow technology. The reaction conditions producing ≥75 % yield were identified by a machine learning approach based on BO. It was demonstrated that BO produced the desired reaction conditions with a small number of experiments (19 and 10 experiments) in the entire search space (10,500 combinations of reaction conditions). Gaussian process (GP) models produced by BO provided the relationships between combinations of reaction parameters and outputs (RCRPO).

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)0.001
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: Methods · Consensus signal: Methods
Teacher disagreement score0.066
Threshold uncertainty score0.943

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.001
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 head0.031
GPT teacher head0.293
Teacher spread0.262 · 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
GenreMethods

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

Citations41
Published2021
Admission routes1
Has abstractyes

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