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Trapping of Active Methylene Intermediates with Alkenes, Indoles or Thiols: Towards Highly Selective Multicomponent Reactions
Author(s) -
Gu Yanlong,
Barrault Joël,
Jérôme François
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900593
Subject(s) - chemistry , methylene , alkene , substrate (aquarium) , indole test , formaldehyde , combinatorial chemistry , thiol , organic chemistry , photochemistry , catalysis , geology , oceanography
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.