Ni-catalyzed alkylative dimerization of vinyl grignard reagents using alkyl fluorides

Jun Terao; Hiroyasu Watabe; Nobuaki Kambe

doi:10.1021/ja042565r

Ni-catalyzed alkylative dimerization of vinyl grignard reagents using alkyl fluorides

J Am Chem Soc. 2005 Mar 23;127(11):3656-7. doi: 10.1021/ja042565r.

Authors

Jun Terao¹, Hiroyasu Watabe, Nobuaki Kambe

Affiliation

¹ Department of Molecular Chemistry & Science and Technology Center for Atoms, Molecules and Ions Control, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan.

PMID: 15771474
DOI: 10.1021/ja042565r

Abstract

Alkyl halides underwent unique cross-coupling reaction with vinylmagnesium chloride in the presence of Ni catalyst to give 2-alkyl-3-butenyl Grignard reagent (1) in high yields. This reaction proceeded efficiently at 25 degrees C in THF using primary and secondary alkyl fluorides. On the other hand, PhCH=CHMgBr gave double alkylative vinyl coupling product 4 in good yield as the sole coupling product. Alkyl fluorides react as the most suitable alkylating reagent in comparison to the corresponding chlorides, bromides, and iodides.