A Method for Palladium-Catalyzed Cross-Couplings of Simple Alkyl Chlorides: Suzuki Reactions Catalyzed by [Pd2(dba)3]/PCy3 dba=(E,E)-dibenzylideneacetone, Cy=cyclohexyl. We thank Dr. Matthew R. Netherton for helpful discussions and Johnson Matthey Inc. for supplying palladium compounds. Support has been provided by the Deutsche Akademie der Naturforscher Leopoldina (Leopoldina fellowship to J.H.K., BMBF-LPD 9901/8-48), Bristol-Myers Squibb, the National Institutes of Health (National Institute of General Medical Sciences, R01-GM62871), the Natural Sciences and Engineering Research Council of Canada (postdoctoral fellowship to C.D.), and Novartis. Funding for the MIT Department of Chemistry Instrumentation Facility has been provided in part by NSF CHE-9808061 and NSF DBI-9729592.
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Bibliographic record
Abstract
The window of reactivity is relatively narrow in the first Suzuki cross-coupling of alkyl chlorides with alkyl 9-borabicyclo[3.3.1]nonane (9-BBN) derivatives catalyzed by [Pd2(dba)3] [Eq. (1); dba=(E,E)-dibenzylideneacetone]: whereas good yields are obtained with the ligand tricyclohexylphosphane for ligands that are appreciably larger or smaller, essentially no coupling is observed. As the conditions are compatible with a variety of functional groups, this method introduces a new class of substrates into the family of potential partners in palladium-catalyzed cross-coupling reactions. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2002/z18905_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
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Full frame distilled prediction
Teacher imitationNot 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.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.005 | 0.004 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.001 | 0.001 |
| Scholarly communication | 0.000 | 0.001 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.000 | 0.000 |
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.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it