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Pd-NHC catalyzed conjugate addition versus the Mizoroki-Heck reaction.

Chemistry (Weinheim an der Bergstrasse, Germany) (2011-02-10)
Aditya L Gottumukkala, Johannes G de Vries, Adriaan J Minnaard
ABSTRACT

Ace of base: A catalytic system is presented that, solely by choice of the base, selectively switches between conjugate addition and the Mizoroki-Heck reaction of aryl halides with Michael acceptors (see scheme; R, R' = alkyl, aryl). For conjugate addition reactions, this avoids the preparation and use of organometallics.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Benzylideneacetone, ≥98%, FG
Sigma-Aldrich
Cesium pivalate, 98%
Sigma-Aldrich
trans-4-Phenyl-3-buten-2-one, ≥99%
Sigma-Aldrich
4-Phenyl-3-buten-2-one, 99%