20125-68-2Relevant academic research and scientific papers
Solvent-modulated Pd/C-catalyzed deprotection of silyl ethers and chemoselective hydrogenation
Ikawa, Takashi,Hattori, Kazuyuki,Sajiki, Hironao,Hirota, Kosaku
, p. 6901 - 6911 (2007/10/03)
Recently we have reported undesirable and frequent deprotection of the TBDMS protective group of a variety of hydroxyl functions occurred under neutral and mild hydrogenation conditions using 10% Pd/C in MeOH. The deprotection of silyl ethers is susceptible to significant solvent effect. TBDMS and TES protecting groups were selectively cleaved in the presence of acid-sensitive functional groups such as TIPS ether, TBDPS ether and dimethyl acetal under hydrogenation condition using 10% Pd/C in MeOH. In contrast, chemoselective hydrogenation of reducible functional groups such as acetylene, olefin and benzyl ether, proceeds in the presence of TBDMS or TES ethers in AcOEt or MeCN.
A remarkable solvent effect toward the Pd/C-catalyzed cleavage of silyl ethers
Sajiki, Hironao,Ikawa, Takashi,Hattori, Kazuyuki,Hirota, Kosaku
, p. 654 - 655 (2007/10/03)
Selective hydrogenation conditions of olefin, benzyl ether and acetylene functionalities in the presence of TBDMS or TES ether have been developed.
