(3+2) Cycloaddition of Heteroaromatic N-Ylides with Sulfenes
Kosuke Yamamoto1, Kohei Torigoe1, Masami Kuriyama1
1Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.
Abstract:
A (3+2) cycloaddition of heteroaromatic N-ylides with sulfenes, which are generated in situ from sulfonyl chlorides, has been developed. A variety of ylides were transformed into the corresponding sulfone-embedded N-fused heterocycles in high yields. Hexafluoroisopropyl mesylate was demonstrated to be a suitable reactant for quinolinium ylides. Furthermore, this cycloaddition could be performed with an ylide prepared by a Cu-catalyzed ylide transfer reaction in a one-pot manner, extending the substrate scope to an unisolable ylide.
More Related Videos
12:07Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Nucleophilic Aromatic Substitution: Elimination–Addition
Cycloaddition Reactions: MO Requirements for Thermal Activation
Preparation and Reactions of Sulfides
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
