Lanthanum trifluoromethanesulfonate is an effective single-component catalyst for synthesizing a variety of amides directly from esters and amines under mild conditions. Highly selective amidation of esters and amines, as well as catalyst-controlled amidation of esters, demonstrated the effectiveness of the catalyst system.
Direct
catalytic alcoholysis of unactivated amides is one of the
most difficult challenges in organic chemistry, and an applicable
method for cleaving amides used as directing groups in regioselective
functionalization reactions has not been reported. Herein, we report
direct catalytic alcoholysis of 8-aminoquinoline amides, which are
highly effective directing groups in regioselective functionalization
reactions. The reactions proceeded with a simple combination of substrates,
air-stable catalysts, and alcohols, affording the corresponding esters
in good yields with broad functional group tolerance. Highly chemoselective
cleavage of the 8-aminoquinoline amides in the presence of related
carbonyl functionalities and preliminary mechanistic studies are also
described.
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