Insight into Transmetalation Enables Cobalt-Catalyzed Suzuki–Miyaura Cross Coupling
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.
Bibliographic record
Abstract
High Resolution Image Download MS PowerPoint Slide Among the fundamental transformations that comprise a catalytic cycle for cross coupling, transmetalation from the nucleophile to the metal catalyst is perhaps the least understood. Optimizing this elementary step has enabled the first example of a cobalt-catalyzed Suzuki–Miyaura cross coupling between aryl triflate electrophiles and heteroaryl boron nucleophiles. Key to this discovery was the preparation and characterization of a new class of tetrahedral, high-spin bis(phosphino)pyridine cobalt(I) alkoxide and aryloxide complexes, ( iPr PNP)CoOR, and optimizing their reactivity with 2-benzofuranylBPin (Pin = pinacolate). Cobalt compounds with small alkoxide substituents such as R = methyl and ethyl underwent swift transmetalation at 23 °C but also proved kinetically unstable toward β–H elimination. Secondary alkoxides such as R = i Pr or CH(Ph)Me balanced stability and reactivity. Isolation and structural characterization of the product following transmetalation, ( iPr PNP)Co(2-benzofuranyl), established a planar, diamagnetic cobalt(I) complex, demonstrating the high- and low-spin states of cobalt(I) rapidly interconvert during this reaction. The insights from the studies in this elementary step guided selection of appropriate reaction conditions to enable the first examples of cobalt-catalyzed C–C bond formation between neutral boron nucleophiles and aryl triflate electrophiles, and a model for the successful transmetalation reactivity is proposed.
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 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 | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.001 |
| 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