2026-10-14T15:39:45Z https://api.figshare.com/v2/oai

oai:figshare.com:article/34027672 2026-09-29T21:05:08Z category_4 category_146 category_7 category_8 category_15 category_19 category_21 category_272 category_873 portal_63 item_type_6 month_year_09_2026

Rapid Deprotection of O- and N‑Benzyl Groups by Catalytic Transfer Hydrogenation with Industrially Viable Silane Reagents Maciej Graużenis (25139041) Teresa Olszewska (2082490) Biochemistry Space Science Medicine Microbiology Neuroscience Pharmacology Biotechnology Environmental Sciences not elsewhere classified Chemical Sciences not elsewhere classified scale reductive cleavage scale industrial syntheses primary aromatic amines intensive purification techniques corresponding deprotected products consistently high yields aromatic azo compounds short reaction times mild reaction conditions scalable deprotection protocol catalytic transfer hydrogenation >- benzyl amines </ italic >- reaction byproducts catalytic system benzyl ethers sustainable alternative readily removed rapid deprotection pmhs ), pharmaceutical applications n </ including extraction donor reagents column chromatography ambient pressure 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. 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. 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. 2026-09-29T00:00:00Z Text Journal contribution 10.1021/acs.oprd.6c00334.s001 https://figshare.com/articles/journal_contribution/Rapid_Deprotection_of_O-_and_N_Benzyl_Groups_by_Catalytic_Transfer_Hydrogenation_with_Industrially_Viable_Silane_Reagents/34027672 CC BY-NC 4.0