γ-Selective Allylation of (E)-Alkenylzinc Iodides Prepared by Reductive Coupling of Arylacetylenes with Alkyl Iodides.
The first examples of Cu-catalyzed γ-selective allylic alkenylation using organozinc reagents are reported. (E)-Alkenylzinc iodides were prepared by Fe-catalyzed reductive coupling of terminal arylalkynes with alkyl iodides. In the presence of a copper catalyst, these reagents reacted with allylic bromides derived from Morita-Baylis-Hillman alcohols to give 1,4-dienes in high yields. The reactions are highly γ-selective (generally γ/α > 49:1) and tolerate a wide range of functional groups such as ester, cyano, keto, and nitro.
Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL) , ISIC-LSCI, BCH 3305, Lausanne 1015, Switzerland.
Fedor E
FE
Zhurkin
Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL) , ISIC-LSCI, BCH 3305, Lausanne 1015, Switzerland.
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Hu