Ni-catalyzed alkylative dimerization of vinyl grignard reagents using alkyl fluorides.
J Am Chem Soc. 2005 Mar 23; 127(11):3656-7.JA

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.

Authors+Show Affiliations

Terao J

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.

Watabe H

No affiliation info available

Kambe N

No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

15771474

Citation

Terao, Jun, et al. "Ni-catalyzed Alkylative Dimerization of Vinyl Grignard Reagents Using Alkyl Fluorides." Journal of the American Chemical Society, vol. 127, no. 11, 2005, pp. 3656-7.

Terao J, Watabe H, Kambe N. Ni-catalyzed alkylative dimerization of vinyl grignard reagents using alkyl fluorides. J Am Chem Soc. 2005;127(11):3656-7.

Terao, J., Watabe, H., & Kambe, N. (2005). Ni-catalyzed alkylative dimerization of vinyl grignard reagents using alkyl fluorides. Journal of the American Chemical Society, 127(11), 3656-7.

Terao J, Watabe H, Kambe N. Ni-catalyzed Alkylative Dimerization of Vinyl Grignard Reagents Using Alkyl Fluorides. J Am Chem Soc. 2005 Mar 23;127(11):3656-7. PubMed PMID: 15771474.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Ni-catalyzed alkylative dimerization of vinyl grignard reagents using alkyl fluorides. AU - Terao,Jun, AU - Watabe,Hiroyasu, AU - Kambe,Nobuaki, PY - 2005/3/18/pubmed PY - 2005/3/18/medline PY - 2005/3/18/entrez SP - 3656 EP - 7 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 127 IS - 11 N2 - 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. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/15771474/Ni_catalyzed_alkylative_dimerization_of_vinyl_grignard_reagents_using_alkyl_fluorides_ DB - PRIME DP - Unbound Medicine ER -

Tags

Ni-catalyzed alkylative dimerization of vinyl grignard reagents using alkyl fluorides.J Am Chem Soc. 2005 Mar 23; 127(11):3656-7.JA