Premium
Ruthenium‐Catalyzed Direct Transformation of Alkenyl Oximes to 5‐Cyanated Isoxazolines: A Cascade Approach Based on Non‐Stabilized Radical Intermediate
Author(s) -
Wang DanJun,
Chen BeiYi,
Wang YiQi,
Zhang XiaoWei
Publication year - 2018
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.201701651
Subject(s) - chemistry , catalysis , ruthenium , combinatorial chemistry , functional group , reagent , ammoxidation , cyanide , radical cyclization , nitro , organic chemistry , alkyl , acrylonitrile , copolymer , polymer
A ruthenium‐catalyzed ammoxidation of alkenyl oximes under mild and neutural condtions is described. In this method, tert ‐butyl nitrite plays a dual role, acting as an oxidant as well as a nitrogen source. This reaction avoids using any toxic radical initiators or cyanide reagents. This convenient and practical method offers an easy access to 5‐cyanated isoxazolines in good to high yields, and shows good functional group tolerance and high efficiency. It is rather remarkable that this new reaction provides a strategically distinct approach based on non‐stabilized radical intermediate and constructs C–O and C≡N triple bonds in a single‐step. Moreover, the difunctionalization of unactivated olefins bearing oximes has been realized.