Tetrahedron
Tetrahedron
5 years ago

Construction of carbocycles initiated by Cu-catalyzed radical reaction of Cl2C(CN)2

Construction of carbocycles initiated by Cu-catalyzed radical reaction of Cl2C(CN)2
A Cu-catalyzed radical reaction of Cl2C(CN)2 was utilized for stereoselective conversion of unsaturated molecules into functionalized carbocycles. Chloromalononitrile radicals, generated by treating Cl2C(CN)2 with catalytic amounts of CuCl and dppf in refluxing dioxane, intermolecularly reacted with the unsaturated bonds of acyclic or 10-membered compounds. The resultant carboradicals then intramolecularly added to another unsaturated bond to produce 1,2-disubstituted cyclopentane or trans-decalin derivatives. The chemo- and stereoselectivities of these radical cascade reactions are discussed in detail.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402017303125

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