Palladium‐Catalyzed Suzuki Couplings of 2,3‐Dibromonorbornadiene: Synthesis of Symmetrical and Unsymmetrical Aryl‐Substituted Norbornadienes
Bibliographic record
Abstract
Abstract Palladium‐catalyzed Suzuki coupling reactions between 2,3‐dibromonorbornadiene and arylboronic acids were investigated. These reactions provide an efficient method for the synthesis of symmetrical 2,3‐diarylnorbornadienes which are not accessible using the traditional Diels–Alder cycloaddition reactions. The optimized reaction conditions of the Suzuki coupling reactions were found using [Pd2(dba)3] (0.5 mol%), tBu3P (1.4 mol%) and CsF in THF. High yields of the Suzuki coupling products were obtained when electron‐rich arylboronic acids were used. On the other hand, Suzuki coupling reactions with electronic‐deficient or sterically hindered arylboronic acids gave lower yields of the corresponding 2,3‐di‐arylnorbornadienes. Unsymmetrical mono‐ and diaryl‐substituted norbornadienes were also prepared in good yields using this method. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot 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.
Distilled classifier scores by category (both heads)
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.001 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.002 | 0.001 |
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.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from itClassification
machine, unvalidatedMachine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.
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".