Single electron transfer-induced cross-coupling reaction of alkenyl halides with aryl Grignard reagents

E Shirakawa, R Watabe, T Murakami…

Index: Shirakawa, Eiji; Watabe, Ryo; Murakami, Takuya; Hayashi, Tamio Chemical Communications, 2013 , vol. 49, # 45 p. 5219 - 5221

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Citation Number: 14

Abstract

The reaction conditions employed in the coupling of aryl halides with aryl Grignard reagents were effectively applied to the reaction of alkenyl halides essentially as they stand (Scheme 1). 3 Thus, 2-naphthylmagnesium bromide (1a: 1.5 equiv.), prepared in THF and then evacuated in vacuo, was heated at 110 °C for 48 h with (E)-1-octenyl iodide ((E)-2m: 1 equiv.) and THF (6 equiv.) in toluene to give (E)-1-(2-naphthyl)-1-octene, (E)-3am, in 90% yield (entry 1). ...