Advances in Copper and Nickel C─N and C─O Cross‐Couplings of (Hetero)Aryl Chlorides Enabled by Ancillary Ligand Development
Bibliographic record
Abstract
The evolution of palladium-catalyzed C─N and C─O cross-coupling chemistry into first-choice methods for the synthesis of aniline and phenol derivatives can be attributed to innovations in ancillary ligand design that facilitate challenging elementary steps of thermal catalysis. Inspired by this strategy, and in the quest to establish more sustainable thermal base metal catalysis that is competitive with and complementary to such precious metal protocols, several successful mechanism-inspired ancillary ligand classes for use in enabling high-performing copper and nickel catalysts have emerged over the last decade. In this Review we document key ancillary ligand advances of this type, with a focus on superlative copper and nickel catalysts that enable C─N or C─O cross-couplings of cheap and abundant (hetero)aryl chloride electrophiles under operationally simple conditions of relevance to end-users in academia and industry.
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How this classification was reachedexpand
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 | 0.001 | 0.000 |
| Meta-epidemiology (narrow) | 0.001 | 0.001 |
| Meta-epidemiology (broad) | 0.001 | 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 | 0.001 |
| 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 itClassification
machine, unvalidatedMachine predicted; a candidate call from one teacher head, 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".