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Substituted Benzenes: The Kirsch Synthesis of Cybrodol

2013· book-chapter· en· W3103892188 on OpenAlexaboutno aff
Douglass F. Taber

Bibliographic record

VenueOxford University Press eBooks · 2013
Typebook-chapter
Languageen
FieldChemistry
TopicCatalytic Cross-Coupling Reactions
Canadian institutionsnot available
Fundersnot available
KeywordsArylChemistryHalideAldehydeCatalysisMedicinal chemistryPolymer chemistryOrganic chemistry

Abstract

fetched live from OpenAlex

Stephen L. Buchwald of MIT established (J. Am. Chem. Soc. 2010, 132, 14076) a Pd-catalyzed protocol for conversion of an aryl triflate 1 to the halide 2. Jie Wu of Fudan University prepared (Tetrahedron Lett. 2010, 51, 6646) aromatic halides from the corresponding carboxylic acids. Yong-Chua Teo of Nanyang Technological University described (Tetrahedron Lett . 2010, 51, 3910) the Mn-mediated conversion of 3 to 5, suggesting a benzyne intermediate. Takanori Shibata of Waseda University effected (Synlett 2010, 2601) the direct Ru-mediated coupling of aryl halides with amines, and Paul Helquist of the University of Notre Dame prepared (J. Org. Chem. 2010, 75, 4887) anilines by coupling aryl halides with NaN3 . Chao-Jun Li of McGill University devised (Tetrahedron Lett. 2010, 51, 5486) the Pd-catalyzed decarbonylative Heck coupling of 6 with 7 to give 8. Mats Larhed of Uppsala University showed (Angew. Chem. Int. Ed. 2010, 49, 7733) that Pd could also catalyze the decarboxylative coupling of an aromatic acid 9 with a nitrile to give the ketone 10. Dennis G. Hall of the University of Alberta found (Tetrahedron Lett. 2010, 51, 4256) that an areneboronic acid could promote the Zr-catalyzed ortho condensation of a phenol 11 with an aldehyde, leading to 12, which could then be carried on to a range of other products. Professor Hall also showed (Angew. Chem. Int. Ed. 2010, 49, 2883) that areneboronic acids are stable to many standard organic transformations, and that the product boronic acids can be readily purified by extraction into sorbitol/Na2CO3. Professor Buchwald reported (J. Am. Chem. Soc. 2010, 132, 14073) an optimized source of Pd for the Suzuki-Miyaura coupling, allowing the room-temperature participation even of unstable boronic acids such as 13. Wing-Yiu Yu of the Hong Kong Polytechnic University observed (J. Am. Chem. Soc. 2010, 132, 12862) that 17 was an effective donor for the Pd-catalyzed ortho C-H amination of 16. Nicholas C. O. Tomkinson of Cardiff University uncovered (Synlett 2010, 2471) the facile rearrangement of 19 to 20. Professor Buchwald described (J. Am. Chem. Soc. 2010, 132, 9990) the coupling of 21, prepared from the aryl halide, with 22 to give the benzofuran 23.

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 score0.008
Threshold uncertainty score0.028

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0010.000
Science and technology studies0.0010.000
Scholarly communication0.0000.001
Open science0.0000.001
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0080.004

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 head0.205
Teacher spread0.182 · 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

Citations0
Published2013
Admission routes1
Has abstractyes

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