Trapping of Active Methylene Intermediates with Alkenes, Indoles or Thiols: Towards Highly Selective Multicomponent Reactions

In this paper, a basic method to access new multicomponent reactions (MCRs) is reported. The mechanism of these MCRs is based on the trapping of methylene intermediates, formed in situ by reaction of formaldehyde with electron‐rich carbons, with alkene, thiol or indole derivatives. According to our...

Full description

Saved in:
Bibliographic Details
Published in:Advanced synthesis & catalysis 2009-12, Vol.351 (18), p.3269-3278
Main Authors: Gu, Yanlong, Barrault, Joël, Jérôme, François
Format: Article
Language:English
Subjects:
formaldehyde
methylene intermediates
multicomponent reaction
tandem reactions
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:In this paper, a basic method to access new multicomponent reactions (MCRs) is reported. The mechanism of these MCRs is based on the trapping of methylene intermediates, formed in situ by reaction of formaldehyde with electron‐rich carbons, with alkene, thiol or indole derivatives. According to our strategy, a wide range of valuable skeletons has been obtained in a one‐pot reaction, thus allowing a minimization of waste, cost and labor. The presented methodology exhibits a broad substrate scope and electron‐rich carbons in the α‐position of a hydroxy or carbonyl group were found to be particularly efficient. More generally, this work offers new tools for creating molecular complexity and diversity from one of the simplest organic building blocks, formaldehyde.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200900593