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通过银介导的分子内氧银化反应实现酰胺芳炔前体的区域选择性芳基化

Regioselective Arylation of Amidoaryne Precursors via Ag-Mediated Intramolecular Oxy-Argentation.

作者信息

Kwon Yong-Ju, Kong Ye-Jin, Lee Min-Jung, Lim Eun-Hye, Kwak Jaesung, Kim Won-Suk

机构信息

Department of Chemistry and Nanoscience, Ewha Womans University, Seoul, 03760, Republic of Korea.

Infectious Diseases Therapeutic Research Center, Korea Research Institute of Chemical Technology (KRICT), Daejeon, 34114, Republic of Korea.

出版信息

Adv Sci (Weinh). 2024 May;11(17):e2308829. doi: 10.1002/advs.202308829. Epub 2024 Feb 25.

DOI:10.1002/advs.202308829
PMID:38403474
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11077674/
Abstract

An unprecedented silver-mediated intramolecular oxy-argentation of 3-amidoaryne precursors that quickly generates a heteroarylsilver species is developed. AgF acts as both a stoichiometric fluoride source and a reagent for the formation of a benzoxazolylsilver intermediate via aryne generation. Pd-catalyzed coupling reactions of (hetero)aryl iodides with a silver species, generated in situ, allow for the synthesis of various C7-arylated benzoxazoles. As a result, an aryl group is selectively introduced into the meta-position of 3-amidobenzyne precursors. Mechanistic studies have indicated the presence of a benzoxazolylsilver intermediate and revealed that the reaction proceeds via an intramolecular oxy-argentation process, which is initiated by a direct fluoride attack on the silyl group.

摘要

开发了一种前所未有的银介导的3-酰胺基芳炔前体的分子内氧银化反应，该反应能快速生成杂芳基银物种。AgF既是化学计量的氟源，也是通过生成芳炔形成苯并恶唑基银中间体的试剂。钯催化（杂）芳基碘与原位生成的银物种的偶联反应，可用于合成各种C7-芳基化苯并恶唑。结果，芳基被选择性地引入到3-酰胺基苯炔前体的间位。机理研究表明存在苯并恶唑基银中间体，并揭示该反应通过分子内氧银化过程进行，该过程由氟直接进攻硅烷基引发。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e929/11077674/fd884e9f5ecc/ADVS-11-2308829-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e929/11077674/3ac817ed92cd/ADVS-11-2308829-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e929/11077674/e64c63fb39a9/ADVS-11-2308829-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e929/11077674/195c527d9ab7/ADVS-11-2308829-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e929/11077674/41e1b64ec0d4/ADVS-11-2308829-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e929/11077674/fd884e9f5ecc/ADVS-11-2308829-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e929/11077674/3ac817ed92cd/ADVS-11-2308829-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e929/11077674/e64c63fb39a9/ADVS-11-2308829-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e929/11077674/195c527d9ab7/ADVS-11-2308829-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e929/11077674/41e1b64ec0d4/ADVS-11-2308829-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e929/11077674/fd884e9f5ecc/ADVS-11-2308829-g003.jpg

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