Aliphatic thioacetate deprotection using catalytic tetrabutylammonium. cyanide

作者：Holmes BT^*; Snow AW

来源：Tetrahedron, 2005, 61(52): 12339-12342.

DOI：10.1016/j.tet.2005.09.092

• thioacetate
• deprotection
• tetrabutylammoniurn cyanide
• thiol

A series of thiol-functionalized organic compounds were selected to analyze the scope and efficiency of a new thioacetate deprotection method using catalytic tetrabutylammonium cyanide (TBACN) to effect the transformation of a thioacetate group to a free thiol in the presence of a protic solvent. Particularly attractive are the mild reaction and workup conditions, reduced byproduct formation typically seen using literature methods and yields of greater than 80% for the free aliphatic thiols. This method is effective on aliphatic thiols with trityl, benzyl, p-halo-benzyl, phenethyl, phenoxyethyl, and cyclohexylethyl structural moieties, but it is not effective with thiophenols. Published by Elsevier Ltd.

• 出版日期2005-12-26