Palladium-Catalyzed Tandem Cycloisomerization/Cross-Coupling of Carbonyl- and Imine-Tethered Alkylidenecyclopropanes

被引：11
|
作者：
Verdugo, Felipe [1 ,2 ]
Rodino, Ricardo [1 ,2 ]
Calvelo, Martin [1 ,2 ]
Mascarenas, Jose Luis [1 ,2 ]
Lopez, Fernando [1 ,2 ,3 ]
机构：
[1] Univ Santiago de Compostela, Ctr Singular Invest Quim Biol & Mat Mol CIQUS, Santiago De Compostela, Spain
[2] Univ Santiago de Compostela, Dept Quim Organ, Santiago De Compostela, Spain
[3] CSIC, Mision Biol Galicia MBG, Pontevedra 36680, Spain
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2022年 / 61卷 / 24期
关键词：
Alkylidenecyclopropanes; Boronic Acids; Cycloisomerization; Palladium Catalysis; Tandem Reaction; 3+2 INTRAMOLECULAR CYCLOADDITION; ETHYL CYCLOPROPYLIDENEACETATE; ALKYNES; ALK-5-YNYLIDENECYCLOPROPANES; ALKENYLIDENECYCLOPROPANES; ALKYNYLIDENECYCLOPROPANES; CARBOCYCLIZATION; TRANSFORMATIONS; TRANSMETALATION; COCYCLIZATION;
D O I：
10.1002/anie.202202295
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Pd-0 catalysts featuring phosphorus-based monodentate ligands can detour the reactivity of carbonyl-tethered alkylidenecyclopropanes (ACPs) from standard (3+2) cycloadditions towards tandem cycloisomerization/cross-coupling processes. This new reactivity lies on the formation of key pi-allyl oxapalladacyclic intermediates, which are subsequently trapped with external nucleophilic partners, instead of undergoing canonical C-O reductive eliminations. Importantly, the use of imine-tethered ACP's is also feasible. Therefore, the method provides a straightforward and stereoselective entry to a wide variety of highly functionalized cyclic alcohols and amines.
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页数：7
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