Unknown

Dataset Information

0

Hypervalent iodine-mediated Ritter-type amidation of terminal alkenes: The synthesis of isoxazoline and pyrazoline cores.

ABSTRACT: Hypervalent iodine-mediated olefin functionalization provides a rapid gateway towards accessing both various heterocyclic cores and functional groups. In this regard, we have developed a Ritter-type alkene functionalization utilizing a PhI(OAc)2 ((diacetoxyiodo)benzene, PIDA)/Lewis acid combination in order to access isoxazoline and pyrazoline cores. Based on allyl ketone oximes and allyl ketone tosylhydrazones, we have developed an alkene oxyamidation and amido-amidation protocol en route to accessing both isoxazoline and pyrazoline cores. Additionally, acetonitrile serves as both the solvent and an amine source in the presence of this PIDA/Lewis acid combination. This operationally straightforward and metal-free protocol provides an easy access to isoxazoline and pyrazoline derivatives.

SUBMITTER: Park SW 

PROVIDER: S-EPMC6009250 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Hypervalent iodine-mediated Ritter-type amidation of terminal alkenes: The synthesis of isoxazoline and pyrazoline cores.

Park Sang Won SW   Kim Soong-Hyun SH   Song Jaeyoung J   Park Ga Young GY   Kim Darong D   Nam Tae-Gyu TG   Hong Ki Bum KB  

Beilstein journal of organic chemistry 20180511

Hypervalent iodine-mediated olefin functionalization provides a rapid gateway towards accessing both various heterocyclic cores and functional groups. In this regard, we have developed a Ritter-type alkene functionalization utilizing a PhI(OAc)<sub>2</sub> ((diacetoxyiodo)benzene, PIDA)/Lewis acid combination in order to access isoxazoline and pyrazoline cores. Based on allyl ketone oximes and allyl ketone tosylhydrazones, we have developed an alkene oxyamidation and amido-amidation protocol en  ...[more]

Similar Datasets

Unknown Thioamination of Alkenes with Hypervalent Iodine Reagents.
| S-EPMC4725223 | biostudies-literature
Unknown Copper-catalyzed aminoalkynylation of alkenes with hypervalent iodine reagents.
| S-EPMC5857935 | biostudies-literature
Unknown Ritter-type iodo(iii)amidation of unactivated alkynes for the stereoselective synthesis of multisubstituted enamides.
| S-EPMC8612402 | biostudies-literature
Unknown Recyclable hypervalent-iodine-mediated solid-phase peptide synthesis and cyclic peptide synthesis.
| S-EPMC6009197 | biostudies-literature
Unknown A unified photoredox-catalysis strategy for C(sp<sup>3</sup>)-H hydroxylation and amidation using hypervalent iodine.
| S-EPMC5635418 | biostudies-literature
Unknown Terminal olefins to linear ?,?-unsaturated ketones: Pd(II)/hypervalent iodine co-catalyzed Wacker oxidation-dehydrogenation.
| S-EPMC4084756 | biostudies-literature
Unknown Oxidation of BINOLs by Hypervalent Iodine Reagents: Facile Synthesis of Xanthenes and Lactones.
| S-EPMC9311707 | biostudies-literature
Unknown Stereoselective Formation of Substituted 1,3-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III).
| S-EPMC6332268 | biostudies-literature
Unknown Facile oxidative rearrangements using hypervalent iodine reagents.
| S-EPMC3922481 | biostudies-literature
Unknown Hypervalent Iodine(III)-Induced Domino Oxidative Cyclization for the Synthesis of Cyclopenta[b]furans.
| S-EPMC6274509 | biostudies-literature