Table · dataset · 2026
Rapid Deprotection of O- and N‑Benzyl Groups by Catalytic Transfer Hydrogenation with Industrially Viable Silane Reagents
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A practical and scalable deprotection protocol for <i>O</i>- and <i>N</i>-benzyl protecting groups has been developed using wet Pd/C and organosilanes, notably 1,1,3,3-tetramethyldisiloxane (TMDS) and poly(methylhydrosiloxane) (PMHS), as hydrogen-donor reagents.
Description
The use of these cost-effective hydrogen sources eliminates the need for molecular hydrogen, significantly improving process safety while providing a rapid and efficient approach to debenzylation.
Operating under mild reaction conditions and ambient pressure, this methodology is designed for pharmaceutical applications where avoiding hazardous gas handling is a priority. The developed system efficiently cleaves benzyl esters, benzyl ethers, and <i>N</i>-benzyl amines, affording the corresponding deprotected products in short reaction times and consistently high yields (82–98%). Importantly, the reaction byproducts can be readily removed by standard industrial unit operations, including extraction, distillation, and crystallization, eliminating the need for labor-intensive purification techniques such as column chromatography.
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Additionally, the utility of the catalytic system was extended to the efficient, gram-scale reductive cleavage of aromatic azo compounds into primary aromatic amines. This operationally simple approach offers a sustainable alternative for both laboratory and large-scale industrial syntheses.
Links
Where it is published
- DOI doi.org/10.1021/acs.oprd.6c00334.s001 ↗
DOI / persistent id · from zivahub uct ac za
Catalogue records · 1
- OAI-PMH record api.figshare.com/v2/oai?verb=GetRecord&metadataPrefix=oai_dc&identifier=oai%3Af… ↗
metadata API · from zivahub uct ac za
Topics
- From keywords
- Astronomy & Astrophysics · Chemistry · Earth & Environmental Science · Engineering · Life Sciences · Medicine & Health · Microbiology
Provenance · 1 source records, 12 field assertions
| Source | Key | Last seen | Raw |
|---|---|---|---|
| ZivaHub | oai:figshare.com:article/34027672 | 13 d ago | JSON v1 |
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| license | source · zivahub uct ac za | connector:zivahub_uct_ac_za@1.0.0 | /metadata/dc/rights |
| publication_date | source · zivahub uct ac za | connector:zivahub_uct_ac_za@1.0.0 | |
| title | source · zivahub uct ac za | connector:zivahub_uct_ac_za@1.0.0 | /metadata/dc/title |