Isolation and Reactions of Imidoyl Fluorides Generated from Oxime Using the Diethylaminosulfur Trifluoride/Tetrahydrofuran (DAST–THF) System
Yipu Lu, Akitomo Kasahara, Tadashi Hyodo, Kazuaki Ohara, Kentaro Yamaguchi, Yuko Otani, Tomohiko Ohwada
Abstract
Fluorination of oximes with the relatively mild diethylaminosulfur trifluoride/tetrahydrofuran (DAST-THF) system affords imidoyl fluorides. These compounds were isolated, and their structures were confirmed by X-ray single-crystal structure analysis. Reaction of imidoyl fluorides with various nucleophiles efficiently afforded amides, amidines, thioamides, and amine derivatives in high yields. Furthermore, one-pot reaction of in situ generated imidoyl fluorides from oximes was also applicable to efficient synthesis of these products. The oxime stereochemistry and acid-labile protecting group remained intact in this system.
Topics & Concepts
ChemistryTetrahydrofuranOximeTrifluorideIsolation (microbiology)Medicinal chemistryCombinatorial chemistryOrganic chemistryBioinformaticsSolventBiologyFluorine in Organic ChemistrySynthesis and Biological EvaluationSynthesis and Reactions of Organic Compounds