[reaction: see text] Neopentyl arenesulfonates were reacted with methyl and primary alkylmagnesium bromides in the presence of dppeNiCl(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.
Palladium-catalyzed cross-coupling reactions of neopentyloxysulfonylphenyl bromides with arylboronic acids provided a variety of neopentyl biphenylsulfonates in good yields. 2-Bromo-and 4-bromobenzenesulfonates underwent the coupling reaction more rapidly than 3-bromobenzenesulfonate, while chlorobenzenesulfonate did not produce the coupling product under the standard reaction conditions.
Sulfonic acids and estersSulfonic acids and esters Q 0550Synthesis of Neopentyl Biphenylsulfonates Using the Suzuki-Miyaura Reaction. -2-, 3-and 4-Bromobenzenesulfonates (I) undergo Pd-catalyzed cross-coupling reactions with arylboronic acids (IV) to provide the title compounds such as (V), (VI) and (VII) in good yields. Similar chlorobenzenesulfonates do not produce the corresponding coupling products. -(CHO, C.-H.; KIM, C.-B.; SUN, M.; PARK*, K.; Bull.
Polyphenyl derivatives Q 0700Nickel-Catalyzed Cross-Coupling of Neopentyl Arenesulfonates with Methyl and Primary Alkylmagnesium Bromides. -The method offers an efficient approach to alkylarenes and indicates that neopentyloxysulfonyl can act as excellent leaving group in Ni-catalyzed reactions. -(CHO, C.-H.; SUN, M.; SEO, Y.-S.; KIM, C.-B.; PARK*, K.; J.
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