- Experimental mechanistic studies of the tail-to-tail dimerization of methyl methacrylate catalyzed by N-heterocyclic carbene
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We and others have previously reported the intermolecular umpolung reactions of Michael acceptors catalyzed by an N-heterocyclic carbene (NHC). The representative tail-to-tail dimerization of methyl methacrylate (MMA) has now been intensively investigated
- Kato, Terumasa,Ota, Yoshiya,Matsuoka, Shin-Ichi,Takagi, Koji,Suzuki, Masato
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p. 8739 - 8747
(2013/09/24)
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- Sequential one-pot and three-component reactions of an N-heterocyclic carbene to form 4-(1,2,4-triazol-5-ylidene)pyrrolidine-2,5-diones: A tandem umpolung/annulation sequence via deoxy-Breslow intermediates
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The tandem sequence of the umpolung of α,β-unsaturated esters by an N-heterocyclic carbene (NHC) followed by annulation is demonstrated. The deoxy-Breslow intermediates are selectively generated from the reaction of NHC with methyl methacrylate, dimethyl itaconate, or methyl crotonate. Subsequently, they undergo annulation with isocyanates to give 4-(1,2,4-triazol-5-ylidene) pyrrolidine-2,5-diones in good isolated yields. In addition, the stoichiometric three-component reaction of NHC, methyl methacrylate, and phenyl isocyanate proceeded, accompanied by the formation of the 1:2 adduct of NHC with phenyl isocyanate.
- Matsuoka, Shin-Ichi,Tochigi, Yusuke,Takagi, Koji,Suzuki, Masato
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p. 9836 - 9841
(2012/11/07)
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