Zincation of Styrylsulfonium Salts

Yamada, Kodai, Kintzel, Mika B., Perry, Gregory J.P., Saito, Hayate and Yorimitsu, Hideki (2022) Zincation of Styrylsulfonium Salts. Organic Letters, 24 (40), 7446-7449. (doi:10.1021/acs.orglett.2c03013).

Record type: Article

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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e-pub ahead of print date: 4 October 2022

Published date: 14 October 2022

Additional Information: Funding Information: This work was supported by JSPS KAKENHI Grant JP19H00895 and JST CREST Grant JPMJCR19R4. M.B.K. is the recipient of a ‘Programme to increase the Mobility of Students from German Universities’ (PROMOS) scholarship. G.J.P.P. is the recipient of a JSPS Postdoctoral Fellowship for Research in Japan (KAKENHI Grant JP21F21039). The authors thank Professor Kohei Kusada and Professor Hiroshi Kitagawa for assistance with XRF analysis. Publisher Copyright: © 2022 American Chemical Society.