Tetrahedron Letters p. 85 - 88 (1981)
Update date:2022-08-05
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Sato, Fumie
Ishikawa, Hiroaki
Sato, Masao
Disubstituted acetylenes react with isobutylmagnesium halide in the presence of a catalytic amount of Cp2TiCl2 in ether to afford E-alkenyl Grignard reagents selectively and in almost quantitative yields.The regiochemistry of this hydromagnesation reaction is high for alkylarylacetylenes and silylacetylenes giving E-ArC(MgBr)=CHR from alkylarylacetylenes, E-ArC(MgBr)=CH(SiMe3) from arylsilylacetylenes, and E-CHR=C(MgBr)(SiMe3) from alkylsilylacetylenes, respectively.Thanks to the high reactivity of the Grignard reagent, the present reaction offers a novel, selective and operationally simple route for preparation of trisubstituted olefins.
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