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Record W4408122796 · doi:10.1021/acs.oprd.4c00477

Continuous Preparation of Trifluoromethyl Diazomethane in Flow Using In-Line Membrane Phase Separation─Application to the Catalytic Asymmetric Cyclopropanation of Substituted Styrenes

2025· article· en· W4408122796 on OpenAlex
Tyler K. Allred, Olga A. Мukhina, Oleg L. Epstein, Jie Yan, Kevin Crossley, Matthew G. Beaver, Michael Frohn, James I. Murray, David Bauer

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.

Bibliographic record

VenueOrganic Process Research & Development · 2025
Typearticle
Languageen
FieldPharmacology, Toxicology and Pharmaceutics
TopicFluorine in Organic Chemistry
Canadian institutionsPivotal (Canada)
FundersAmgen
KeywordsCyclopropanationDiazomethaneTrifluoromethylCatalysisChemistryPhase (matter)MembraneFlow (mathematics)Line (geometry)ChromatographyOrganic chemistryCombinatorial chemistryPhysicsMechanicsMathematics

Abstract

fetched live from OpenAlex

Trifluoromethyl diazomethane (TFDM) is a versatile reagent in organic synthesis and medicinal chemistry efforts. The utility of TFDM is hampered by safety concerns on scale. A novel method for the generation of dry, acid-free concentrated solutions of TFDM in a flow is reported here. The inclusion of an in-line liquid–liquid phase separator was a critical component in the flow scheme. The resulting dry stream could be coupled to a reactor containing a chiral ruthenium catalyst and styrene substrate to enantioselectively construct trans -trifluoromethyl-substituted cyclopropanes in a plug flow reactor–batch train. This system was utilized to access a variety of enantioenriched trans -trifluoromethyl-substituted cyclopropanes.

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.

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)0.004
metaresearch head score (Gemma)0.002
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: Empirical · Consensus signal: Empirical
Teacher disagreement score0.046
Threshold uncertainty score0.692

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0040.002
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0010.007
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0000.001
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 head0.099
GPT teacher head0.521
Teacher spread0.422 · 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