Different Reaction Patterns in the Baylis-Hillman Reaction of Aryl Aldehydes with Phenyl Vinyl Ketone, Phenyl Acrylate and Phenyl Thioacrylate

Molecules

Min Shi¹  Chao-Qun Li¹ 

[1] State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 China

关键词: Baylis-Hillman reaction;    Lewis base;    Phenyl vinyl ketone (PVK);    Phenyl acrylate;    DABCO;    Conjugate addition;    DMAP;   

DOI  :  10.3390/71000721

来源: mdpi

【 摘 要 】

In the Baylis-Hillman reaction of aryl aldehydes with phenyl vinyl ketone we have observed exclusive formation of diadducts 4, and that the yields of diadduct can reach 80% with increasing amounts of phenyl vinyl ketone. On the other hand, for phenyl acrylate and phenyl thioacrylate, only the normal Baylis-Hillman adduct was obtained. The effects of substituents were also examined and a plausible reaction mechanism is proposed for the formation of compounds 4.

【 授权许可】

CC BY   
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