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N , N′ ‐Dimethylated Benzyloxytriazinedione: A Stable Solid Reagent for Acid‐Catalyzed O ‐Benzylation
Author(s) -
Fujita Hikaru,
Kakuyama Satoshi,
Kunishima Munetaka
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601387
Subject(s) - chemistry , reagent , catalysis , coproduct , organic chemistry , trifluoromethanesulfonate , acylation , triazine , solid acid , medicinal chemistry , mathematics , pure mathematics
N , N′ ‐Dimethylated 6‐(benzyloxy)‐1,3,5‐triazine‐2,4(1 H ,3 H )‐dione (DMBOT) has been developed as a triazinedione‐based, stable solid reagent for acid‐catalyzed O ‐benzylation. The conceptual basis of the design was to fix the core triazinedione skeleton, and the two methyl groups in positions 1 and 3 were introduced to acheive this. The coproduct of DMBOT can be easily removed by simple washing. Various acid‐ and base‐labile alcohols were O ‐benzylated by using DMBOT in the presence of an acid catalyst. In particular, 2,6‐di‐ tert ‐butylpyridinium trifluoromethanesulfonate, which is a mild, stable, and nonhygroscopic acid catalyst, can be used with DMBOT for this reaction. Compared to other reported methods, DMBOT gave better results for several challenging O ‐benzylation reactions under nonbasic conditions.