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2002•European Journal of Organic ChemistryRequires access

Lewis Base Effects in the Baylis−Hillman Reaction of Imines with Methyl Vinyl Ketone

Min Shi, Yongmei Xu

Open publisher page 70 citations

Abstract

In the Baylis−Hillman reaction of N-benzylidene-4-methylbenzenesulfonamide with methyl vinyl ketone (MVK), we found that, in the presence of a catalytic amount of DMAP, PPh3 or DABCO as Lewis base, the Baylis−Hillman reaction can be greatly accelerated to give the normal Baylis−Hillman adducts 1 in good or very high yields. However, with PBu3 as a Lewis base, the abnormal Baylis−Hillman adducts 2 and 3 were formed under the same reaction conditions. The effect of the substituents was also examined and a plausible reaction mechanism proposed.

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What this paper is about

In the Baylis−Hillman reaction of N-benzylidene-4-methylbenzenesulfonamide with methyl vinyl ketone (MVK), we found that, in the presence of a catalytic amount of DMAP, PPh3 or DABCO as Lewis base, the Baylis−Hillman reaction can be greatly accelerated to give the normal Baylis−Hillman adducts 1 in good or very high yields. However, with PBu3 as a Lewis base, the abnormal Baylis−Hillman adducts 2 and 3 were formed under the same reaction conditions. The effect of the substituents was also examined and a plausible reaction mechanism proposed.

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OpenAlex reports 70 citations for this work. Citation counts describe recorded attention and do not establish research quality.

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Available abstract

In the Baylis−Hillman reaction of N-benzylidene-4-methylbenzenesulfonamide with methyl vinyl ketone (MVK), we found that, in the presence of a catalytic amount of DMAP, PPh3 or DABCO as Lewis base, the Baylis−Hillman reaction can be greatly accelerated to give the normal Baylis−Hillman adducts 1 in good or very high yields. However, with PBu3 as a Lewis base, the abnormal Baylis−Hillman adducts 2 and 3 were formed under the same reaction conditions. The effect of the substituents was also examined and a plausible reaction mechanism proposed.

Key concepts: DABCO, Methyl vinyl ketone, Chemistry, Baylis–Hillman reaction, Lewis acids and bases, Adduct, Ketone, Catalysis

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