Regioselective/electro-oxidative intermolecular [3 + 2] annulation for the preparation of indolines
Qingqing Wang1, Pan Wang1, Xinlong Gao1
1College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University Wuhan 430072 P. R. China hengzhang@whu.edu.cn aiwenlei@whu.edu.cn.
Abstract:
Compared with the reported intramolecular electro-oxidative cyclization of alkenyl amines or vinyl anilines for the preparation of pyrrolidines or indolines, the intermolecular version is less studied. Herein, this electrochemical intermolecular oxidative annulation of anilines and alkenes for the preparation of indolines proceeded under external oxidant-free conditions. The most noteworthy achievement of our work is the facile generation of indolines with quaternary centers at the 2-position. In addition, alkenes and anilines bearing various functional groups can be well tolerated. Remarkably, electrolyte-free conditions were used in an electrochemical flow cell, which shows the application potential of this method.
Related Concept Videos
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Regioselectivity of Electrophilic Additions-Peroxide Effect
Cycloaddition Reactions: Overview
Regioselective Formation of Enolates
Thermal Electrocyclic Reactions: Stereochemistry
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...

![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
