Skeletal Modification of Tryptophan Using Cyclic Diaryliodonium Salts via Palladium-Catalyzed Cascade π-Extended Annulative Dual C2–H/N–H Arylation

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-10-15 DOI:10.1021/acs.orglett.6c03837

Sowmya B. Udayakumar,Kiranmai Nayani

引用次数: 0

Abstract

Abstract We have demonstrated an efficient Pd-catalyzed annulative dual C2–H/N–H arylation reaction involving modification of the tryptophan indole skeleton to phenanthridinyl indole. This is an operationally simple and ligand-free strategy that was extended to biologically important indole derivatives and tryptophan-containing short peptides to deliver a diverse unnatural phenanthridinyl indole-tethered peptide with good efficiency. Notably, the method demonstrated good tolerance for N- and C-terminal protecting groups as well as for the side-chain functionalities of other amino acids.

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钯催化级联π扩展环双C2-H / N-H芳基化对环二芳基盐对色氨酸的骨架修饰

摘要：我们已经证明了一个有效的pd催化的环状双C2-H / N-H芳基化反应，包括将色氨酸吲哚骨架修饰为苯基吲哚。这是一种操作简单且无配体的策略，可扩展到具有重要生物学意义的吲哚衍生物和含色氨酸的短肽中，以高效率地递送多种非天然的苯基吲哚系链肽。值得注意的是，该方法对N和c端保护基团以及其他氨基酸的侧链功能具有良好的耐受性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.