A novel strategy has been developed for the synthesis of 2,3‐diarylindanones and 2‐arylindenes through the formation of trisubstituted α,β‐unsaturated esters by the ring opening of 2,3‐diarylcyclopropenones in the presence ofa catalytic amount of TPP under mild reaction conditions. Initially, PPh3 activates the diarylcyclopropenone to generate the phosphonium adduct, which simultaneously reacts with 4‐hydroxycoumarins to afford the α,β‐unsaturated esters instead of Wittig olefination. Subsequently, these α,β‐unsaturated esters undergo a smooth Friedel‐Crafts type cyclization with arenes in the presence of AlCl3 to give a new series of 2,3‐diarylindanones in good to excellent yields. Additionally, the reduction of α,β‐unsaturated esters with NaBH4 followed by the acid catalyzed cyclization of resulting allylic alcohols afforded the 2‐arylindenes in good yields. This is the first report on the use of α,β‐unsaturated esters as precursors for diarylindanones and arylindenes synthesis.

中文翻译：

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从高张力 2,3-二芳基环丙烯酮和香豆素衍生物衍生的三取代 α,β-不饱和酯合成 2,3-二芳基茚酮和 2-芳基茚

开发了一种合成 2,3-二芳基茚酮和 2-芳基茚的新策略，通过 2,3-二芳基环丙烯酮在催化量的 TPP 存在下在温和条件下开环形成三取代的 α,β-不饱和酯。反应条件。最初，PPh3 活化二芳基环丙烯酮生成鏻加合物，同时与 4-羟基香豆素反应生成 α,β-不饱和酯，而不是维蒂希烯化。随后，这些 α,β-不饱和酯在 AlCl3 存在下与芳烃进行顺利的 Friedel-Crafts 型环化，得到一系列新的 2,3-二芳基茚酮，产率良好至优异。此外，用 NaBH4 还原 α,β-不饱和酯，然后进行酸催化环化所得烯丙醇，以良好的产率提供 2-芳基茚。这是关于使用 α,β-不饱和酯作为二芳基茚酮和芳基茚合成前体的第一份报告。