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多氟芳烃与官能化、掩蔽芳基亲核试剂的无过渡金属偶联反应

Transition-Metal-Free Coupling of Polyfluorinated Arenes and Functionalized, Masked Aryl Nucleophiles.

作者信息

Finck Lucie, Oestreich Martin

机构信息

Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623, Berlin, Germany.

出版信息

Chemistry. 2021 Aug 2;27(43):11061-11064. doi: 10.1002/chem.202101731. Epub 2021 Jun 10.

DOI:10.1002/chem.202101731
PMID:34014007
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8453572/
Abstract

A chemoselective C(sp )-C(sp ) coupling of sufficiently electron-deficient fluorinated arenes and functionalized N-aryl-N'-silyldiazenes as masked aryl nucleophiles is reported. The fluoride-promoted transformation involves the in situ generation of the aryl nucleophile decorated with various sensitive functional groups followed by a stepwise nucleophilic aromatic substitution (S Ar). These reactions typically proceed at room temperature within minutes. This catalytic process allows for the functionalization of both coupling partners, furnishing highly fluorinated biaryls in good yields.

摘要

报道了一种化学选择性的C(sp²)-C(sp²)偶联反应，该反应涉及电子充分缺电子的氟化芳烃与作为掩蔽芳基亲核试剂的官能化N-芳基-N'-硅基重氮化合物。氟化物促进的转化过程包括原位生成带有各种敏感官能团的芳基亲核试剂，随后进行逐步亲核芳香取代（S Ar）。这些反应通常在室温下几分钟内即可完成。这种催化过程使得两个偶联伙伴都能实现官能化，以良好的产率提供高度氟化的联芳基化合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b00/8453572/5f6e1d8342b8/CHEM-27-11061-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b00/8453572/969d2b346c38/CHEM-27-11061-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b00/8453572/6400c2cd3b52/CHEM-27-11061-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b00/8453572/9196c95066af/CHEM-27-11061-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b00/8453572/5f6e1d8342b8/CHEM-27-11061-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b00/8453572/969d2b346c38/CHEM-27-11061-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b00/8453572/6400c2cd3b52/CHEM-27-11061-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b00/8453572/9196c95066af/CHEM-27-11061-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b00/8453572/5f6e1d8342b8/CHEM-27-11061-g002.jpg

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