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温和条件下杂芳烃的无金属选择性单卤代羧基化反应

Metal-free selective mono-halodecarboxylation of heteroarenes under mild conditions.

作者信息

Henderson Scott H, West Ryan A, Ward Simon E, Honey Mark A

机构信息

Sussex Drug Discovery Centre, University of Sussex, Brighton BN1 9RH, UK.

Medicines Discovery Institute, Cardiff University, Park Place CF10 3AT, UK.

出版信息

R Soc Open Sci. 2018 Jun 20;5(6):180333. doi: 10.1098/rsos.180333. eCollection 2018 Jun.

Abstract

The halodecarboxylation of heteroarene carboxylic acids by treatment with -bromosuccinimide or -chlorosuccinimide was performed. This procedure provides a convenient route to synthetically useful mono-halogenated heteroarene intermediates such as halo-indoles, -aza-indoles, -indazoles and -aza-indazoles. The mild conditions employed and simple protocol provides an advantage over traditional halodecarboxylation procedures that require expensive and toxic metal catalysts, basic conditions, time-consuming intermediate isolation and elevated reaction temperatures.

摘要

通过用 N-溴代琥珀酰亚胺或 N-氯代琥珀酰亚胺处理来进行杂芳烃羧酸的卤代脱羧反应。该方法为合成有用的单卤代杂芳烃中间体,如卤代吲哚、氮杂吲哚、吲唑和氮杂吲唑,提供了一条便捷途径。所采用的温和条件和简单方案相对于传统的卤代脱羧方法具有优势,传统方法需要昂贵且有毒的金属催化剂、碱性条件、耗时的中间体分离以及较高的反应温度。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7bbb/6030312/40ad3f5f445e/rsos180333-g1.jpg

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