Synlett 2023; 34(18): 2165-2168
DOI: 10.1055/a-2089-4260
cluster
Modern Boron Chemistry: 60 Years of the Matteson Reaction

Chemo-, Regio-, and Stereoselective Access to (E)-Boryl-Substituted Allyl Fluorides via Electrophilic Fluorodesilylation

Yongsuk Jung
,
Seung Hwan Cho
This work was supported by a National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIT) (Grant no. NRF-2022R1A2C3004731). Y.J. thanks the NRF for a Ph.D. fellowship (NRF-2021R1A6A3A13038576).


Abstract

Herein, we report a transition-metal-free chemo-, regio-, and stereoselective electrophilic fluorodesilylation of α-silyl-substituted allylboronate esters. α-Silyl-substituted allylboronate esters can be chemoselectively coupled with Selectfluor, resulting in a variety of (E)-boryl-substituted allyl fluorides in good yields with γ- and (E)-selectivities. The utilities of the obtained (E)-boryl-substituted allyl fluorides are highlighted by further modifications to afford allyl or alkyl fluoride derivatives.

Supporting Information



Publication History

Received: 20 April 2023

Accepted after revision: 09 May 2023

Accepted Manuscript online:
09 May 2023

Article published online:
14 June 2023

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