Gorbunova Yelizaveta, Ryabukhin Dmitry S, Vasilyev Aleksander V
Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, 199034, Russia.
All-Russia Research Institute for Food Additives - Branch of V.M. Gorbatov Federal Research Center for Food Systems of RAS, Liteyniy pr., 55, Saint Petersburg, 191014, Russia.
Beilstein J Org Chem. 2021 Nov 1;17:2663-2667. doi: 10.3762/bjoc.17.180. eCollection 2021.
Reactions of 3-arylpropynenitriles (ArC≡CCN) with electron-rich arenes (Ar'H, benzene and its polymethylated derivatives) under the action of aluminum bromide (AlBr, 6 equiv) at room temperature for 0.5-2 h result in the stereoselective formation of 3,3-diarylpropenenitriles (Ar(Ar')C=CHCN) in yields of 20-64%, as products of mainly hydroarylation of the acetylene bond. The obtained 3,3-diarylpropenenitriles in triflic acid CFSOH (TfOH) at room temperature for 1 h are cyclized into 3-arylindenones in yields of 55-70%.
在室温下，3-芳基丙炔腈（ArC≡CCN）与富电子芳烃（Ar'H、苯及其多甲基化衍生物）在溴化铝（AlBr，6当量）作用下反应0.5 - 2小时，以20 - 64%的产率立体选择性地生成3,3-二芳基丙烯腈（Ar(Ar')C=CHCN），这是乙炔键主要氢芳基化的产物。将所得的3,3-二芳基丙烯腈在室温下于三氟甲磺酸CF₃SO₃H（TfOH）中反应1小时，环化生成3-芳基茚酮，产率为55 - 70%。
