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Synthesis of Functionalized Nitriles by Microwave‐Promoted Fragmentations of Cyclic Iminyl Radicals
Author(s) -
Jackman Mary M.,
Im Siyeon,
Bohman Seth R.,
Lo Concordia C. L.,
Garrity Amanda L.,
Castle Steven L.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201705728
Subject(s) - radical , chemistry , reagent , cyanide , oxime , adduct , ring (chemistry) , substrate (aquarium) , microwave , combinatorial chemistry , medicinal chemistry , photochemistry , organic chemistry , oceanography , physics , quantum mechanics , geology
The synthesis of functionalized nitriles via microwave‐promoted radical fragmentations of cyclic O ‐phenyl oxime ethers is reported. A variety of radical traps can be employed, permitting the generation of diverse adducts via C−O, C−C, C−N, or C−X bond formation. Other salient features include a simple and practical protocol, very short reaction times, and the avoidance of metal catalysts and toxic cyanide reagents. The utility of this method is demonstrated by the ring‐distortion of a steroid‐derived substrate.