4-Aminobenzotriazole (ABTA) as a Removable Directing Group for Palladium-Catalyzed Aerobic Oxidative C–H Olefination

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2022-03-24 DOI:10.1021/acs.orglett.2c00285

Zhuo Wang, Xiaohan Ye, Meina Jin, Qi Tang, Shengyu Fan, Zhiguang Song* and Xiaodong Shi*,

引用次数: 1

Abstract

4-Aminobenzotriazole (ABTA) was applied as an effective removable directing group (DG) in Pd-catalyzed C–H activation for the first time. Compared with the widely applied pyridine and quinoline analogs, ABTA showed significantly improved reactivity, achieving aerobic oxidative C–H olefination in excellent yields (up to 95% vs <50% with other reported DGs under identical conditions). Using this new strategy, macrocyclization was achieved to give cyclic peptides in good yields with easy ABTA removal under mild conditions, highlighting the promising potential of this new DG.

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4-氨基苯并三唑(ABTA)作为钯催化烃类烯烃好氧氧化的可移动导向基团

4-氨基苯并三唑(ABTA)首次作为一种有效的可移动导向基团(DG)应用于pd催化的C-H活化。与广泛应用的吡啶和喹啉类似物相比，ABTA表现出显著提高的反应活性，以优异的收率(高达95%，而其他报道的DGs在相同条件下的收率为50%)实现了烃类烯烃的有氧氧化。利用这种新策略，实现了大环化，在温和的条件下容易去除ABTA，以高产量获得环肽，突出了这种新DG的潜力。

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.