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Zincation of Styrylsulfonium Salts
Kodai Yamada1, Mika B Kintzel1, Gregory J P Perry1
1Department of Chemistry, Graduate School of Science, Kyoto University, Kyoto 606-8502, Japan.
Abstract:
We report the formation of zinc reagents by the reaction of styrylsulfonium salts with zinc powder. Transition metals and other additives are not required for promoting zincation. Zincation tolerates a variety of sensitive functional groups, including esters, bromides, and boronic esters, and proceeds with complete retention of stereochemistry. This method presents a practical approach to the formation of zinc reagents that can be used in a variety of functionalizations, such as halogenation, carboxylation, and Negishi cross-couplings.
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