氮和膦路易斯碱催化芳醛与N-磺化亚胺与乙炔二甲酸二甲酯的反应。
Reactions of arylaldehydes and N-sulfonated imines with dimethyl acetylenedicarboxylate catalyzed by nitrogen and phosphine lewis bases.
作者信息
Li Chao-Qun, Shi Min
机构信息
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
出版信息
Org Lett. 2003 Nov 13;5(23):4273-6. doi: 10.1021/ol0354324.
[reaction: see text] In the reaction of arylaldehydes or N-sulfonated imines (0.5 mmol) with dimethyl acetylenedicarboxylate (DMAD) (0.6 mmol) catalyzed by pyridine or DMAP (20 mol %), we found that (E)-2-aryl-but-2-enedioic acid dimethyl ester 1 or (E)-2-[aryl-(toluene-4-sulfonylimino)methyl]-but-2-enedioic acid dimethyl ester 2 was formed in good yields at 60 degrees C in THF. A plausible mechanism has been proposed.
[反应：见正文] 在吡啶或4-二甲氨基吡啶（DMAP）（20摩尔%）催化下，芳醛或N-磺酰亚胺（0.5毫摩尔）与乙炔二甲酸二甲酯（DMAD）（0.6毫摩尔）的反应中，我们发现（E）-2-芳基-2-丁烯二酸二甲酯1或（E）-2-[芳基-（对甲苯磺酰亚氨基）甲基]-2-丁烯二酸二甲酯2在60℃的四氢呋喃中能以良好的产率生成。已提出了一个合理的反应机理。
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