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Combined Catalytic System of Scandium Triflate and Boronic Ester for Amide Bond Cleavage
Author(s) -
Kita Yusuke,
Nishii Yuji,
Onoue Akihiro,
Mashima Kazushi
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300819
Subject(s) - scandium , chemistry , trifluoromethanesulfonate , amide , catalysis , cleavage (geology) , boronic acid , organic chemistry , bond cleavage , combinatorial chemistry , polymer chemistry , geotechnical engineering , fracture (geology) , engineering
We have found that the combination of scandium with boronic ester enables the cleavage of amide bonds. Primary amides were converted to the corresponding esters in the presence of catalytic amounts of scandium triflate and boronic ester under mild and neutral conditions. This unique catalytic system can be applied to the deprotection of acetylaniline derivatives. In addition, control NMR experiments were carried out to examine the effect of the boronic esters.