Issue 13, 2023

Formal allylic C(sp3)–H alkylation of α-alkylstyrenes by rearrangement of intermediate alkenyl sulfonium salts

Abstract

Metal-free allylic C(sp3)–H alkylation of α-alkylstyryl sulfonium salts based on [2,3]-sigmatropic rearrangement strategies has been developed. This operationally simple protocol enables allylic C(sp3)–H alkylation of a wide range of α-alkylstyryl sulfonium salts. Notably, this method could allow facile access to allylated carbon quaternary centers in moderate to good yields. The one-pot procedure, product derivatization and late-stage functionalization all show the potential practicality of this protocol in organic synthesis.

Graphical abstract: Formal allylic C(sp3)–H alkylation of α-alkylstyrenes by rearrangement of intermediate alkenyl sulfonium salts

Supplementary files

Article information

Article type
Research Article
Submitted
29 Mar 2023
Accepted
27 May 2023
First published
27 May 2023

Org. Chem. Front., 2023,10, 3275-3279

Formal allylic C(sp3)–H alkylation of α-alkylstyrenes by rearrangement of intermediate alkenyl sulfonium salts

Z. Shao, J. Zhou, Z. Wang, B. Liu, L. Zou, C. Wang and J. Wen, Org. Chem. Front., 2023, 10, 3275 DOI: 10.1039/D3QO00459G

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