Development of the Inverse Sonogashira Reaction for DEL Synthesis

An efficient approach for aryl acetylene DNA-encoded library (DEL) synthesis was developed in this study by transition-metal-mediated inverse Sonogashira reaction of 1-iodoalkyne with boronic acid under ambient conditions, with moderate to excellent conversions and broad substrate adaptability for t...

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Bibliographic Details
Published in:ACS medicinal chemistry letters 2023-03, Vol.14 (3), p.270-277
Main Authors: Luo, Ayun, Zhou, Hongxia, Hua, Qini, An, Yufang, Ma, Hangke, Zhao, Xue, Yang, Kexin, Hu, Yun Jin
Format: Article
Language:English
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Summary:An efficient approach for aryl acetylene DNA-encoded library (DEL) synthesis was developed in this study by transition-metal-mediated inverse Sonogashira reaction of 1-iodoalkyne with boronic acid under ambient conditions, with moderate to excellent conversions and broad substrate adaptability for the first time. Compared to palladium-phosphine, copper iodide performed better in the on-DNA inverse Sonogashira reaction. Interestingly, substrate diversity can be enhanced by first interrogating coupling reagents under copper-promoted conditions, and then revalidating them under palladium-facilitated conditions for those reagents which failed under the former. This complementary validation strategy is particularly well-fitted to any DEL validation studies.
ISSN:1948-5875
1948-5875
DOI:10.1021/acsmedchemlett.2c00477