Pd-Catalyzed Cascade Cyclization by Intramolecular Heck Insertion of an Allene–Allylic Amination Sequence: Application to the Synthesis of 3,4-Fused Tricyclic Indoles

A novel Pd-catalyzed cascade cyclization by intramolecular Heck insertion of an allene–allylic amination sequence was developed. Allenes tethered to ortho-iodoaniline derivatives at the meta-position were reacted with 5–10 mol % of Pd catalyst and 4 equiv of K2CO3 in DMSO at 90 °C, producing 3,4-fus...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2015-06, Vol.17 (11), p.2622-2625
Main Authors: Nakano, Shun-ichi, Inoue, Naoya, Hamada, Yasumasa, Nemoto, Tetsuhiro
Format: Article
Language:English
Subjects:
Amination
Catalysis
Cyclization
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Organometallic Compounds - chemistry
Palladium - chemistry
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:A novel Pd-catalyzed cascade cyclization by intramolecular Heck insertion of an allene–allylic amination sequence was developed. Allenes tethered to ortho-iodoaniline derivatives at the meta-position were reacted with 5–10 mol % of Pd catalyst and 4 equiv of K2CO3 in DMSO at 90 °C, producing 3,4-fused tricyclic 3-alkylidene indoline derivatives in moderate to excellent yield. The reaction products were divergently transformed into three types of 3,4-fused tricyclic indole derivatives, successfully demonstrating the versatile properties of the reaction products.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b00973