Xanthopinacol Boronate: A Robust, Photochemically Assembled and Cleavable Boronic Ester for Orthogonal Chemistry
Bibliographic record
Abstract
Organoboronic acids impact numerous fields of application from organic synthesis to drug discovery and materials science. However, their highly polar nature makes them challenging to handle, purify, and characterize. Boronic esters help overcome these issues, and pinacol esters (Bpin) have become the dominant boronic acid surrogate in organic synthesis. Despite its popularity, Bpin is not without drawbacks. Its formation from pinacol is intrinsically reversible in the presence of water or alcohols, which may cause premature release leading to losses during reactions and purification. This reversibility complicates the hydrolytic regeneration of free boronic acids, which often requires additional steps to destroy the pinacol by-product. Although other boronyl protecting groups exist, their removal requires harsh pH conditions. To address these issues, we developed xanthopinacol boronates (Bxpin), a robust protecting group for boronic acids with excellent orthogonality in various chemical reactions and mild irreversible removal under catalyzed photoredox conditions. Xpin boronates can be obtained directly by irradiation of a mixture of free boronic acid and xanthone with UV light, causing an in situ dimerization of xanthone to the required xanthopinacol. The unique attributes of xpin boronates were further studied by UV-vis spectrophotometry, X-ray crystallography, cyclic voltammetry, and various stability tests.
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.
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) | 0.001 | 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 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| 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".