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Metal‐Catalyzed Synthesis of Functionalized 1,2,4‐Oxadiazoles from Silyl Nitronates and Nitriles
Author(s) -
Nikodemiak Paul,
Koert Ulrich
Publication year - 2017
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.201601378
Subject(s) - silylation , chemistry , trifluoromethanesulfonate , nitrile , cycloaddition , aryl , catalysis , silanol , medicinal chemistry , organic chemistry , alkyl , combinatorial chemistry
The metal‐catalyzed cycloaddition of silyl nitronates and nitriles leading to 1,2,4‐oxadiazoles is described. Silver(I) triflate (AgOTf) and and ytterbium(III) triflate [Yb(OTf) 3 ] are suitable catalysts. A variety of functional groups is tolerated in the nitrile. The reaction works well for alkenyl and aryl silyl nitronates while the use of alkyl silyl nitronates is less efficient. Mechanistic studies are in favour of an elimination of tert ‐butyl(dimethyl)silanol (TBSOH) after the cycloaddition step. The new approach has also been applied for the synthesis of the drug ataluren.