Synthesis of Functionalized Nitriles by Microwave-Promoted Fragmentations of Cyclic Iminyl Radicals.

Autor: Jackman MM; Department of Chemistry and Biochemistry, Brigham Young University, Provo, UT, 84602, USA., Im S; Department of Chemistry and Biochemistry, Brigham Young University, Provo, UT, 84602, USA., Bohman SR; Department of Chemistry and Biochemistry, Brigham Young University, Provo, UT, 84602, USA., Lo CCL; Department of Chemistry and Biochemistry, Brigham Young University, Provo, UT, 84602, USA., Garrity AL; Department of Chemistry and Biochemistry, Brigham Young University, Provo, UT, 84602, USA., Castle SL; Department of Chemistry and Biochemistry, Brigham Young University, Provo, UT, 84602, USA.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2018 Jan 12; Vol. 24 (3), pp. 594-598. Date of Electronic Publication: 2017 Dec 22.
DOI: 10.1002/chem.201705728
Abstrakt: 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.
(© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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