ChemInform Abstract: Undesirable Deprotection of O-TBDMS Groups by Pd/C-Catalyzed Hydrogenation and Chemoselective Hydrogenation Using a Pd/C(en) Catalyst.

Abstract In general, O -TBDMS protective groups have been believed to be stable toward Pd/C-catalyzed hydrogenation conditions. In practice, however, frequent and unexpected loss of the TBDMS protective group of a variety of hydroxyl functions occurred under neutral and mild hydrogenation conditions using 10% Pd/C in MeOH. When a 10% Pd/C–ethylenediamine complex catalyst [10% Pd/C(en)] was used instead of 10% Pd/C, the undesirable problem was perfectly overcome and the chemoselective hydrogenation of reducible functionalities leaving intact the TBDMS protective group was achieved.