S-C Linkage for Allylsulfonximines via BF-Mediated Allylation.

Org Lett

State Key Laboratory of Molecular and Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R. China.

Published: August 2023

A SuFEx linkage reaction between sulfonimidoyl fluoride and allyltrimethylsilane was achieved for the construction of -modified allylsulfoximines in minutes with BF as a nonmetal difunctional activator enabling the activation of both S-F and C-Si bonds to forge the S-C (sp) bond swiftly. Mechanistic studies and DFT calculations indicated that the linkage was initiated with the activation of sulfonimidoyl fluoride and then followed with the transfer of the fluoride anion to the TMS group.

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http://dx.doi.org/10.1021/acs.orglett.3c01902DOI Listing

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