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Hydrosilanes Are Not Always Reducing Agents for Carbonyl Compounds, II: Ruthenium‐Catalyzed Deprotection of tert ‐Butyl Groups in Carbamates, Carbonates, Esters, and Ethers
Author(s) -
Hanada Shiori,
Yuasa Akihiro,
Kuroiwa Hirotaka,
Motoyama Yukihiro,
Nagashima Hideo
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901279
Subject(s) - chemistry , catalysis , ruthenium , reagent , cleavage (geology) , lewis acids and bases , cleave , bond cleavage , organic chemistry , medicinal chemistry , combinatorial chemistry , geotechnical engineering , fracture (geology) , engineering , enzyme
Hydrosilanes act as a reagent to cleave the C–O bond of O t Bu groups in carbamates, carbonates, esters, and ethers by catalysis of a triruthenium cluster. The reaction offers a novel deprotection method for O t Bu groups under neutral conditions, showing unique selectivities that have never been accomplished with conventional Brønsted or Lewis acidic promoters. Possible mechanisms for C–O cleavage are discussed on the basis of NMR spectroscopic analysis.