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Pd-C-induced catalytic transfer hydrogenation with triethylsilane.

トリエチルシランとPd-Cを用いた接触移動水素化反応による多様な官能基の還元

other in vitro not assessed

Abstract

This study demonstrates that in situ molecular hydrogen generation is achievable by combining triethylsilane with a palladium-charcoal catalyst. Under mild and neutral reaction conditions, the generated hydrogen facilitates rapid and efficient reduction of multiple bonds, azide groups, imines, and nitro groups. Additionally, deprotection of benzyl and allyl protecting groups proceeds effectively under the same conditions. The approach offers a practical method for catalytic transfer hydrogenation in synthetic organic chemistry without requiring external hydrogen gas supply.

Mechanism

Triethylsilane reacts with palladium-charcoal catalyst to generate molecular hydrogen in situ, which then drives reduction of multiple bonds, azides, imines, and nitro groups, as well as deprotection of benzyl and allyl groups under neutral conditions.

Bibliographic

Authors
Mandal PK, McMurray JS
Journal
J Org Chem
Year
2007 (2007-08-17)
PMID
17630799
DOI
10.1021/jo0706123

Tags

Delivery context

This is basic research at the cellular or molecular level. For human application, inhalation is the most promising delivery route, but inhalation carries explosion risk and concentration matters (empirical LFL of 10%; high-concentration devices are not recommended).

Safety notes

This is basic research at the cellular or molecular level. For human application, inhalation is the most promising delivery route, but inhalation carries explosion risk and concentration matters (empirical LFL of 10%; high-concentration devices are not recommended).

See also:

Cite as: H2 Papers — PMID 17630799. https://h2-papers.org/en/papers/17630799
Source: PubMed PMID 17630799