Electrochemical Synthesis of (Aza)indolines via Dehydrogenative [3+2] Annulation: Application to Total Synthesis of (±)‐Hinckdentine A

An electrochemical synthesis of functionalized (aza)indolines through dehydrogenative [3+2] annulation of arylamines with tethered alkenes has been developed. Previous reported syntheses through similar inter‐ and intramolecular annulation reactions required noble‐metal catalysts and are mostly limi...

Full description

Saved in:
Bibliographic Details
Published in:Chinese journal of chemistry 2018-10, Vol.36 (10), p.909-915
Main Authors: Hou, Zhong‐Wei, Yan, Hong, Song, Jin‐Shuai, Xu, Hai‐Chao
Format: Article
Language:English
Subjects:
Alkenes
Amines
annulation
Catalysis
Catalysts
Chemical reactions
Chemical synthesis
Dehydrogenation
Dienes
Electrochemistry
Heterocyclic compounds
hinckdentine A
indoline
Organic chemistry
Organic compounds
radical
Well construction
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:An electrochemical synthesis of functionalized (aza)indolines through dehydrogenative [3+2] annulation of arylamines with tethered alkenes has been developed. Previous reported syntheses through similar inter‐ and intramolecular annulation reactions required noble‐metal catalysts and are mostly limited to terminal alkenes or 1,3‐dienes. The electrosynthesis employs the easily available and inexpensive ferrocene as the molecular catalyst and is compatible with di‐, tri‐ and even tetrasubstituted alkenes to construct indolines as well as the more challenging azaindolines. Employing the newly developed electrosynthesis as a key step, the total synthesis of marine alkaloid (±)‐hinckdentine A has been achieved in 12 steps (longest linear sequence) from commercially available materials.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.201800301