Metathesis Reaction of Diazo Compounds and para-Quinone Methides for C–C Double Bond Formation: Synthesis of Tetrasubstituted Alkenes and Quinolinones

The para-quinone methides (p-QMs) are activated by Lewis acid and then attacked by diazo compounds. The following rearrangement leads to nitrogen gas extrusion and C–C double bond formation to constitute a metathesis reaction process. Therefore, the diazoester is transformed into tetrasubstituted alkenes, whereas the diazo-oxindole delivers the quinolinone products. Furthermore, the 13C-labeling experiments were also conducted to elucidate a possible mechanism.

对醌甲基化物（para-quinone methides, p-QMs）经路易斯酸（Lewis acid）活化后，会被重氮化合物（diazo compounds）进攻。后续发生的重排反应将伴随氮气脱除与碳碳双键的形成，进而构成复分解反应过程。在此转化过程中，重氮酯可转化为四取代烯烃，而重氮氧化吲哚则生成喹啉酮类产物。此外，本研究还开展了13C同位素标记实验（13C-labeling experiments），以阐明该反应的潜在机理。