Chemoselective Approach to Versatile Acyl Fluorides by Photoinduced Activation of p‑Methoxybenzyl Esters

Chemoselective Approach to Versatile Acyl Fluorides by Photoinduced Activation of p‑Methoxybenzyl Esters

A new strategy for the metal-free photoinduced activation of p-methoxybenzyl esters is developed using Selectfluor and benzil for the generation of acyl fluoride intermediates that enable various transformations. The highlight of this activation method is its high chemoselectivity in the presence of...

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Veröffentlicht in:Organic letters 2024-09, Vol.26 (37), p.7956-7960
Hauptverfasser: Jeong, Hee-Chan, Lee, Hyo-Jun, Maruoka, Keiji
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amides
chemoselectivity
peptides
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container_title Organic letters
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creator Jeong, Hee-Chan
Lee, Hyo-Jun
Maruoka, Keiji
description A new strategy for the metal-free photoinduced activation of p-methoxybenzyl esters is developed using Selectfluor and benzil for the generation of acyl fluoride intermediates that enable various transformations. The highlight of this activation method is its high chemoselectivity in the presence of other functionalities, such as esters, amides, and ketones. A synthetic application for the preparation of peptide mimetics that possess two different amide units is also described.
doi_str_mv 10.1021/acs.orglett.4c03008
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subjects amides
chemoselectivity
peptides
title Chemoselective Approach to Versatile Acyl Fluorides by Photoinduced Activation of p‑Methoxybenzyl Esters
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