校園頭條

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化學系江建緯助理教授發表最新期刊論文

Late-Stage Photoredox C-H Amidation of N-Unprotected Indole Derivatives: Access to N-(indol-2-yl)amides

作者：Yue Weng, Bo Ding, Yunqing Liu, Chunlan Song, Lo-Ying Chan, and Chien-Wei Chiang

Organic Letters (SCI)

卷數：23 期數：7

頁碼：2710-2714

出版日期：Apr. 2021

Abstract

The late-stage functionalization of N-unprotected indoles can be useful for modifying low-molecular-weight drugs and bioactive peptides. Whereas indole carboxamides are valuable in pharmaceutical applications, the preparation N-(indol-2-yl)- amides with similar structures continues to be challenging. Herein we report on visible-light-induced late-stage photoredox C−H amidation with N-unprotected indoles and tryptophan-containing peptides, leading to the formation of N-(indol-2-yl)amide derivatives. N-Unprotected indoles and aryloxyamides that contain an electron-withdrawing group could be coupled directly to eosin Y as the photocatalyst by irradiation with a green light-emitting diode at room temperature. Mechanistic studies and density functional theory calculations indicate that the transformation might proceed through the oxidative C−H functionalization of indole with a PS* to PS•− cycle. This protocol provides a new toolkit for the late-stage modification labeling and peptide−drug conjugation of N-unprotected indole derivatives.

Keywords

Photoredox catalysis, C−H Activation, Tryptophan bioconjugation, Late-stage modification, Peptides

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