Direct Deoxygenative Homocoupling of Alcohols to Access C(sp<sup>3</sup>)–C(sp<sup>3</sup>) Bonds via Synergistic Ruthenium/Nickel Catalysis
Bibliographic record
Abstract
With an ever-increasing emphasis on green synthesis of chemicals, there has been growing interest in deoxygenative conversion of alcohols as widely available organic feedstocks for chemical synthesis. However, the effective construction of the C(sp 3 )–C(sp 3 ) bond via the direct homocoupling of simple alcohols is still challenging, due to the involvement of multistep reaction processes. Herein, we propose a general strategy for the direct deoxygenative coupling of alcohols via the synergetic catalysis of earth-abundant nickel and ruthenium, using hydrazine as a mediator. This protocol features the in situ formation of carbonyl intermediates via Ru-catalyzed alcohol dehydrogenation, followed by deoxygenative homocoupling to construct the C(sp 3 )–C(sp 3 ) bond under Ni catalysis. The successful C(sp 3 )-O bond cleavage of alcohol does not require a hydrogen acceptor, and only environmentally friendly byproducts (nitrogen, hydrogen, and water) are generated. The method is particularly effective for benzyl alcohols with broad substrate scope and for late-stage elaborations of complex biological molecules, exemplifying the efficiency and practicability of the system.
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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) | 0.000 | 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 | 0.001 |
| Open science | 0.000 | 0.001 |
| Research integrity | 0.000 | 0.001 |
| Insufficient payload (model declined to judge) | 0.001 | 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".