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用于小分子和DNA编码文库合成的醇衍生苯甲酸酯与吡啶的无金属脱氧偶联反应

Metal-free deoxygenative coupling of alcohol-derived benzoates and pyridines for small molecules and DNA-encoded libraries synthesis.

作者信息

Kolusu Sai Rohini Narayanan, Nappi Manuel

机构信息

Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS), Departamento de Química Orgánica, Universidade de Santiago de Compostela Rúa de Jenaro de la Fuente, s/n, 15705 Santiago de Compostela A Coruña Spain

出版信息

Chem Sci. 2022 May 10;13(23):6982-6989. doi: 10.1039/d2sc01621d. eCollection 2022 Jun 15.

Abstract

Alcohols are among the most widely occurring functional groups found in naturally abundant, biologically relevant organic compounds, which in many cases are considered feedstock chemicals. Herein, we report a metal-free method for the deoxygenative coupling of alcohol-derived benzoates and pyridines promoted by visible light. Given the practical, mild and water-compatible conditions, small molecules and DNA headpieces can be successfully functionalized with a range of primary, secondary and tertiary alcohols. This protocol is distinguished by its wide substrate scope and broad applicability, even in the context of late-stage functionalization and DNA-drug coupling reactions.

摘要

醇类是天然丰富的、具有生物相关性的有机化合物中最广泛存在的官能团之一,在许多情况下,这些有机化合物被视为原料化学品。在此,我们报道了一种由可见光促进的醇衍生苯甲酸酯与吡啶的脱氧偶联无金属方法。鉴于其实际、温和且与水兼容的条件,小分子和DNA头部片段可以用一系列伯醇、仲醇和叔醇成功实现功能化。该方案的特点是底物范围广、适用性强,即使在后期功能化和DNA-药物偶联反应的背景下也是如此。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1eef/9200129/8a3c8c491428/d2sc01621d-f1.jpg

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