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Catalytic Silane‐Reduction of Carboxylic Esters and Lactones: Selective Synthetic Methods to Aldehydes, Lactols, and Ethers via Silyl Acetal Intermediates
Author(s) -
Hosokawa Satomi,
Toya Motoki,
Noda Ariki,
Morita Masato,
Ogawa Takaki,
Motoyama Yukihiro
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201703033
Subject(s) - chemistry , silylation , acetal , catalysis , silane , organic chemistry , silanes , carboxylic acid , palladium , hydrolysis , medicinal chemistry
Practical procedures for the production of aldehydes, lactols, and ethers are offered by the palladium‐catalyzed silane‐reduction of carboxylic esters and lactones. The partial reduction of carboxylic esters or lactones with 1,1,3,3‐tetramethyldisiloxane in the presence of commercially available palladium on carbon (Pd/C) and some copper compounds as a co‐catalyst smoothly proceeds under mild conditions to afford the silyl acetal derivatives in high yields, which are easily converted to the corresponding aldehydes or lactols by hydrolysis of silyloxy group. On the other hand, deoxygenated ethers are obtained with high selectivity by treatment of silyl acetals with catalytic amounts of Me 3 SiOTf at –78 °C or stoichiometric amounts of BF 3 •OEt 2 at ambient temperature.