CROSS-COUPLING OF TERTIARY ALKYL GRIGNARD REAGENTS WITH Β-Bromostyrene CATALYZED BY DICHLORO[1,1′-BIS(DIPHENYLPHOSPHINO)FERROCENE]NICKEL(II)

Abstract

Dichloro[1,1′-bis(diphenylphosphino)ferrocene]nickel(II) was found to be an effective catalyst for the cross-coupling of tert-butylmagnesium chloride with β-bromostyrene to give β-tert-butylstyrene selectively.

Zinc Borates: Functionalized Hard Nucleophiles for Coupling Reactions with Secondary Allylic Acetates

“…The nickel catalysts NiCl 2 (PPh 3 ) 2 , NiCl 2 (dppf) were prepared according to the literature methods. [32,33] Boronate esters 1 with R ϭ Ph, MeC 6 H 4 , MeOC 6 H 4 , 2-furyl, and (E)-and (Z)-CHϭCHC 5 H 11 were prepared by the literature procedures. [20,34] Organic extraction products were routinely dried over MgSO 4 and concentrated using a rotary evaporator to leave a residual oil, which was purified by chromatography on silica gel.…”

Arylation of 8-Acetoxyoctalenone in a Nickel-Catalyzed Coupling Reaction with Lithium Arylborates

“…Ϫ The nickel catalysts NiCl 2 (tpp) 2 , NiCl 2 (dppf) were prepared according to the literature methods. [15,16] Boronate esters 12aϪc of Ar ϭ Ph, p-MeC 6 H 4 , and p-MeOC 6 H 4 were prepared by the literature procedures, [8] while 12d,e were prepared by the procedure described below. ∆ 1(9) -Octalone-2 (3) was prepared by the literature method.…”

Nickel Catalyzed Coupling of Organic Halides and Related Reactions

“…134 The catalytic activity of the phosphine modified catalysts is apparently more dependent upon the structure of the Grignard reagent than upon that of the organic halide and results for a selection of ligands are shown in Table 4. 149 Reduction is also observed on treating allyl alcohols with «-propylmagnesium bromide 132 and has been used in the stereospecific conversion of tetrasubstituted alkoxysilanes into trisubstituted silanes (equation 82 The coupling reaction proceeds readily with aryl, alkynyl, alkenyl and allyl halides and that with aryl halides has been extended to polyhalobenzene, condensed aromatic compounds and sterically hindered systems (equations [83][84][85][86][87]. However in some cases, e.g.…”