Generation and Use of Bicyclo[1.1.0]butyllithium under Continuous Flow Conditions

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-20 DOI:10.1021/acs.orglett.5c0070510.1021/acs.orglett.5c00705

Elena Graziano, Marco Colella, Marcus Baumann* and Renzo Luisi*,

引用次数: 0

Abstract

The bicyclo[1.1.0]butyl scaffold has emerged as a valuable bioisostere in drug discovery programs. Here, we present a streamlined approach for the generation of bicyclo[1.1.0]butyllithium and its functionalization with various classes of electrophiles in a one-flow process, eliminating the need for intermediate isolation. In comparison to traditional batch processes, the flow method allows the use of a single organolithium reagent instead of two and operates at significantly higher temperatures (0 °C versus −78 °C), enhancing both practicality and scalability.

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连续流动条件下双环[1.1.0]丁基锂的生成与使用

双环[1.1.0]丁基支架已成为药物发现项目中有价值的生物同分异构体。在这里，我们提出了一种简化的方法来生成双环[1.1.0]丁基锂，并在一流过程中与各种类型的亲电试剂进行功能化，从而消除了中间分离的需要。与传统的批处理工艺相比，流动法允许使用一种有机锂试剂而不是两种，并且在更高的温度（0°C与- 78°C）下工作，增强了实用性和可扩展性。

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.