Activation of <i>gem</i>-Dichloroacetamides and Epoxides Using Elemental Sulfur and Amines: A Route to Monothiooxalamides and α-Ketothioamides
Bibliographic record
Abstract
High Resolution Image Download MS PowerPoint Slide The selective activation of C–X bonds to generate value-added products via transition metal-free methodologies remains a formidable challenge in modern synthetic chemistry. Herein, we report a metal-free didechlorinative strategy for the construction of unsymmetrical monothiooxalamides through C–S and C–N bond formation. This transformation proceeds via a one-pot functionalization of gem -dichloroacetamides with various amines and elemental sulfur (S 8 ) under ambient conditions in an open-air atmosphere, offering a sustainable and operationally simple approach. Additionally, a regioselective epoxide ring-opening approach was implemented using I 2 /DMSO, enabling the efficient synthesis of α -ketothioamides through the incorporation of S 8 and diverse amine nucleophiles. Furthermore, ligand studies revealed that monothiooxalamides exhibit high efficacy as ligands in Cu-catalyzed C–N cross-coupling reactions. The method’s synthetic utility was further demonstrated through gram-scale synthesis and the preparation of natural product derivatives and drug analogues, highlighting its potential for industrial applications.
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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 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.001 | 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 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".