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Organocatalytic Oxidative Cyclization of Amidoximes for the Synthesis of 1,2,4‐Oxadiazolines
Author(s) -
Soni Vineet Kumar,
Kim Jun,
Cho Eun Jin
Publication year - 2018
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.201800238
Subject(s) - chemistry , tetrafluoroborate , electrophile , catalysis , oxidative phosphorylation , combinatorial chemistry , organocatalysis , photocatalysis , photochemistry , medicinal chemistry , organic chemistry , enantioselective synthesis , ionic liquid , biochemistry
Organocatalytic synthesis of bi‐ and tricyclic fused 1,2,4‐oxadiazolines is reported. The reaction proceeds through oxidative cyclization of the corresponding amidoxime using 2,4,6‐tris(4‐fluorophenyl)pyrylium tetrafluoroborate (T( p ‐F)PPT) as the organocatalyst, and molecular oxygen as the green oxidant. During the transformation, T( p ‐F)PPT acts as both the electrophilic catalyst and photocatalyst, and the reaction is promoted by irradiation with visible light. The method introduced herein offers a straightforward route to the preparation of 1,2,4‐oxadiazolines with different functionalities, and is highly atom economical.