By Min Shi, Feijun Wang, Mei-Xin Zhao, Yin Wei, James J Spivey
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Additional resources for The Chemistry of the Morita-Baylis-Hillman Reaction
52 O S 2 X = 4,4'-, 3,3'-C6H4-C6H4 33 Morita–Baylis–Hillman Reaction For polynuclear aromatic aldehydes, the reactivity decreases in the order benzaldehyde41-naphthaldehyde49-anthraldehyde. 114 Heteroaromatic aldehydes are excellent electrophiles in the MBH reaction because of their increased electrophilicity. 0 equiv) R2 R1 N OH O R2 aq. 56 DABCO. 116 The diﬀerence in reactivity of the formyl group present at diﬀerent positions within a heterocyclic system for the MBH reaction has been developed.
80). Subsequently, multicomponent reactions were less explored. In 1998, Richter and Jung30 reported a three-component reaction of a polymer-bound acrylate, aldehydes and sulfonamides in the presence of DABCO as catalyst in dioxane. 81). 82). In the presence of DABCO or 3-HQD as catalyst, together with La(OTf)3 and molecular sieves, the aza-MBH adducts 215 were obtained in moderate to high yields in propan-2-ol. Regarding the choice of base, DABCO was generally recommended since better chemoselectivities were obtained with this catalyst.
Norbornane-2,3-dione (165), an apparently logical candidate for testing, was reported to be unstable,143 which undoubtedly contributed to the unsatisfactory results obtained on attempting the MBH rection with acrylonitrile (8% yield of adduct). None of the conjugated aryl diones 1,2naphthoquinone (166), acenaphthenequinone (167) and 164 were suﬃciently reactive to aﬀord a satisfactory yield of MBH adduct with acrylonitrile and acrolein. 69). 70 Ninhydrin and isatin derivatives, as the electrophilic component in the MBH reaction, readily react with acrylates,145 acrylonitrile,145 1-benzopyran-4(4H)one94 and conjugated nitroalkenes81a to give good to excellent yields of the corresponding adducts (Chapter 2).