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Intramolecular Cyclopropanation of Active Methylene Derivatives Based on FeCl 2 or FeCl 3 -Promoted Radical-Polar Crossover Reactions.

Authors :
Yoshioka E
Imoto Y
Yamaoka Y
Ikeda T
Takahashi H
Tanaka R
Hayashi N
Miyabe H
Source :
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Jun 25; Vol. 30 (36), pp. e202400602. Date of Electronic Publication: 2024 Jun 03.
Publication Year :
2024

Abstract

Radical-polar crossover reactions were studied for the intramolecular cyclopropanation of active methylene derivatives. In the presence of FeCl <subscript>3</subscript> as a stoichiometric oxidant and K <subscript>2</subscript> HPO <subscript>4</subscript> as a base, the dehydrogenative cyclopropanation of active methylenes proceeded through the FeCl <subscript>3</subscript> -promoted oxidative radical cyclization followed by the ionic cyclization to give the bicyclic cyclopropanes. The use of α-chloro-active methylenes leads the subcatalytic cyclopropanation involving two redox pathways. In the presence of K <subscript>2</subscript> HPO <subscript>4</subscript> , the redox cyclopropanation proceeded by using FeCl <subscript>2</subscript> (20 mol%) in combination with ligand (20 mol%).<br /> (© 2024 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)

Details

Language :
English
ISSN :
1521-3765
Volume :
30
Issue :
36
Database :
MEDLINE
Journal :
Chemistry (Weinheim an der Bergstrasse, Germany)
Publication Type :
Academic Journal
Accession number :
38658317
Full Text :
https://doi.org/10.1002/chem.202400602