Rhenium-Catalyzed Arylation–Acyl Cyclization between Enol Lactones and Organomagnesium Halides: Facile Synthesis of Indenones
Binjing Hu1,+, Xinyi Cheng1,+, Ying Hu1, Xingchen Liu1, Konstantin Karaghiosoff2, and Jie Li1,*（李杰）
1 Key Laboratory of Organic Synthesis of Jiangsu Province,College of Chemistry, Chemical Engineering and Materials Science,Soochow University,Ren-Ai Road 199, 215123 Suzhou (P. R. China)
2 Department Chemie, Ludwig-Maximilians-Universitat Mfnchen
Butenandtstrasse 5–13, Haus F, 81377 Munich (Germany)
+ These authors contributed equally to this work.
Angew. Chem. Int. Ed.2021, 60, 15497--15502
A set of rhenium-catalyzed arylation–acyl cyclizations between (hetero)arylmagnesium halides and enol lactones through a cascade C(sp2)−C(sp2)/C(sp2)−C(sp2) bond formation under mild reaction conditions has been developed. Indeed, a wide range of functional groups on both organomagnesium halides and enol lactones is well tolerated by the simple rhenium catalysis, thus furnishing polyfunctionalized indenones in one-pot fashion and with complete control of the regioselectivity. Moreover, this approach also provides a straightforward synthetic route to neolignan and (iso)pauciflorol F. Mechanistic studies demonstrated that the reaction involves a sequence of syn-carborhenation and intramolecular nucleophilic addition.
链接：https://onlinelibrary.wiley.com/doi/full/10.1002/anie.202103465