Boronate Formation-Triggered Azide–Alkyne Cycloaddition

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-18 DOI:10.1021/acs.orglett.5c00732

Jumpei Taguchi, Yohei Ohata, Honoka Akimoto, Hitomi Tabuchi, Kazunobu Igawa, Katsuhiko Tomooka, Takashi Niwa, Takamitsu Hosoya

引用次数: 0

Abstract

A catalyst-free triazole formation reaction between o-borylaryl azides and N-propargyldiethanolamine derivatives is reported. Control experiments demonstrated that the triazole formation was triggered by boronate formation, which brought the azido group and alkyne moiety into close proximity. This boronate formation-triggered azide–alkyne cycloaddition (BAAC) reaction exhibited orthogonality to other azide–alkyne cycloaddition reactions, enabling sequential double-click conjugations with diazido or dialkyne compounds.

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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.