The Chemistry of the Morita-Baylis-Hillman Reaction by Min Shi, Feijun Wang, Mei-Xin Zhao, Yin Wei, James J Spivey

By Min Shi, Feijun Wang, Mei-Xin Zhao, Yin Wei, James J Spivey

Carbon-carbon bond formations and useful workforce differences are the main basic reactions for the development of molecular frameworks and are on the leading edge of natural chemistry study. The Morita-Baylis-Hillman (MBH) style reactions own the 2 most vital specifications - atom financial system and new release of multi-functional teams. the decade has visible exponential development of the MBH response and its functions. in reality, it's already the most robust carbon-carbon bond-forming tools common in natural synthesis. because the Nineteen Nineties, a growing number of learn teams have initiated paintings on diversified points of the MBH response. those have interested by the scope of the substrates, novel catalysts (especially chiral catalysts), response mechanisms, and artificial purposes. therefore, there's now a necessity for a reference detailing the chemistry of this crucial response. This exact publication summarizes the MBH response, aza-MBH response and uneven MBH/aza-MBH response together with the most recent learn and mechanistic investigations. It offers an entire evaluation of MBH-type reactions aimed toward man made natural chemists of all degrees inside of academia and undefined. The chapters hide the; beginning and development of the Morita-Baylis-Hillman response; reactant sessions and response stipulations; catalytic mechanisms; achiral and chiral catalytic platforms; variations of sensible teams; use of Morita-Baylis-Hillman adducts and derivatives as beginning fabrics to build compounds with carbocyclic or heterocyclic frameworks, and the functions of the MBH response in synthesizing typical products.

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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).

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