82947-13-5Relevant articles and documents
Molecular Engineering of β-Substituted Oxoporphyrinogens for Hydrogen-Bond Donor Catalysis
Chahal, Mandeep K.,Payne, Daniel T.,Matsushita, Yoshitaka,Labuta, Jan,Ariga, Katsuhiko,Hill, Jonathan P.
, p. 82 - 90 (2020)
A new class of bifunctional hydrogen-bond donor organocatalyst using oxoporphyrinogens having increased intramolecular hydrogen-bond donor distances is reported. Oxoporphyrinogens are highly non-planar rigid macrocycles containing a multiple hydrogen bond-forming binding site. In this work, we describe the first example of non-planar OxPs as hydrogen-bond donor catalysts prepared using a molecular engineering approach of the binding site for dual activation of substrates. The introduction of β-substituents is key to the catalytic activity and the catalysts are able to catalyze 1,4-conjugate additions and sulfa-Michael additions, as well as, Henry and aza-Henry reactions at low catalyst loadings (≤ 1 mol-%) under mild conditions. Preliminary mechanistic studies have been carried out and a possible reaction mechanism has been proposed based on the bi-functional activation of both substrates through hydrogen-bonding interactions.
Bifunctional organocatalysis with squaramide-containing Dawson organo-polyoxotungstates
Lachkar, David,Lac?te, Emmanuel
, p. 113 - 116 (2016/03/22)
Two squaramide-containing organo-polyoxometalates (POMs) have been prepared, which efficiently catalyze the addition of dicarbonyl derivatives onto nitroolefins. The POM surface enhances the reactivity of the squaramide, and the hybrid acts as a bifunctio
Catalyst-free and solvent-free Michael addition of 1,3-dicarbonyl compounds to nitroalkenes by a grinding method
Xie, Zong-Bo,Wang, Na,Wu, Ming-Yu,He, Ting,Le, Zhang-Gao,Yu, Xiao-Qi
, p. 534 - 538 (2012/06/29)
An environmentally benign, fast and convenient protocol has been developed for the Michael addition of 1,3-dicarbonyl compounds to β-nitroalkenes in good to excellent yields by a grinding method under catalyst- and solvent-free conditions.