524698-47-3Relevant academic research and scientific papers
Nickel-catalyzed cross-coupling of neopentyl arenesulfonates with methyl and primary alkylmagnesium bromides
Cho, Chul-Hee,Sun, Myungchul,Seo, Yong-Seok,Kim, Chul-Bae,Park, Kwangyong
, p. 1482 - 1485 (2007/10/03)
(Chemical Equation Presented) Neopentyl arenesulfonates were reacted with methyl and primary alkylmagnesium bromides in the presence of dp-peNiCl 2, via the nucleophilic aromatic substitution of neopentyloxysulfonyl groups by the primary alkyl nucleophiles, to produce the corresponding alkylarenes in good yields. This result shows that the alkyloxysulfonyl group might be a suitable alternative to halides and triflate in some circumstances.
Nickel(0)-catalyzed cross-coupling of alkyl arenesulfonates with aryl Grignard reagents
Cho, Chul-Hee,Yun, Hee-Sung,Park, Kwangyong
, p. 3017 - 3025 (2007/10/03)
The nickel-catalyzed cross-coupling reactions of neopentyl arenesulfonates with arylmagnesium bromides, involving nucleophilic aromatic substitution of alkyloxysulfonyl groups by aryl nucleophiles, take place in high yields. Optimal efficiencies are obtained by adding 3 + 2 equiv of the Grignard reagent to a mixture of dppfNiCl2 and the sulfonate in refluxing THF. Neopentyl arenesulfonates are useful sources of the electrophilic aryl groups in these transition metal-catalyzed cross-coupling reactions. Aryl sulfonates are inappropriate due to their ambident reactivity under the reaction conditions. This new cross-coupling reaction can be used for the creative elimination of alkyloxysulfonyl groups from aromatic compounds and for the preparation of unsymmetric terphenyls and oligophenyls.
