Ultrasound-Assisted Remote Benzylic C(sp3)–H Alkylation of N-Fluoroamides with Enol Silanes DOI
Boyi Wang, Tianyu Lu, Ziyu Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16473 - 16484

Published: Nov. 7, 2024

We have developed an ultrasound-assisted remote benzylic C(sp3)–H alkylation of N-fluorobenzamides with enol silanes; a series β-aryl substituted propiophenones was generated in good to high yields. This reaction represents formal C(sp3)–C(sp3) coupling and features simplicity, efficiency, wide substrate scope multiple-step sequential process, which involves N–F homolysis, 1,5-hydrogen atom transfer, radical addition, oxidation by copper(II) salt, removal the trimethylsilyl group. Also, DFT theoretical calculations Marcus theory were employed consolidate proposed mechanism.

Language: Английский

Ultrasound-Assisted Remote Benzylic C(sp3)–H Alkylation of N-Fluoroamides with Enol Silanes DOI
Boyi Wang, Tianyu Lu, Ziyu Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16473 - 16484

Published: Nov. 7, 2024

We have developed an ultrasound-assisted remote benzylic C(sp3)–H alkylation of N-fluorobenzamides with enol silanes; a series β-aryl substituted propiophenones was generated in good to high yields. This reaction represents formal C(sp3)–C(sp3) coupling and features simplicity, efficiency, wide substrate scope multiple-step sequential process, which involves N–F homolysis, 1,5-hydrogen atom transfer, radical addition, oxidation by copper(II) salt, removal the trimethylsilyl group. Also, DFT theoretical calculations Marcus theory were employed consolidate proposed mechanism.

Language: Английский

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