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钯催化芳基(拟)卤化物的硼化反应及其在联芳基合成中的应用。

Palladium-catalyzed borylation of aryl (pseudo)halides and its applications in biaryl synthesis.

作者信息

Ji Hong, Cai Jianghong, Gan Nana, Wang Zhaohua, Wu Liyang, Li Guorong, Yi Tao

机构信息

Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences & the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, 511436, People's Republic of China.

School of Basic Sciences, Guangzhou Medical University, Guangzhou, 511436, People's Republic of China.

出版信息

Chem Cent J. 2018 Dec 19;12(1):136. doi: 10.1186/s13065-018-0510-6.

DOI:10.1186/s13065-018-0510-6
PMID:30564982
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6768141/
Abstract

A facile and efficient palladium-catalyzed borylation of aryl (pseudo)halides at room temperature has been developed. Arylboronic esters were expeditiously assembled in good yields and with a broad substrate scope and good functional group compatibility. This approach has been successfully applied to the one-pot two-step borylation/Suzuki-Miyaura cross-coupling reaction, providing a concise access to biaryl compounds from readily available aryl halides. Furthermore, a parallel synthesis of biaryl analogs is accomplished at room temperature using the strategy, which enhances the practical usefulness of this method.

摘要

已开发出一种在室温下简便高效的钯催化芳基(拟)卤化物硼化反应。芳基硼酸酯能快速以良好产率组装而成,具有广泛的底物范围和良好的官能团兼容性。该方法已成功应用于一锅两步硼化/铃木-宫浦交叉偶联反应,可从易得的芳基卤化物简洁地制备联芳基化合物。此外,利用该策略在室温下完成了联芳基类似物的平行合成,提高了该方法的实际应用价值。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cd17/6768141/17083443f6bf/13065_2018_510_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cd17/6768141/ee55a681b3c1/13065_2018_510_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cd17/6768141/17083443f6bf/13065_2018_510_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cd17/6768141/ee55a681b3c1/13065_2018_510_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cd17/6768141/17083443f6bf/13065_2018_510_Sch2_HTML.jpg

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Recent developments in the Suzuki-Miyaura reaction: 2010-2014.铃木-宫浦反应的近期进展:2010 - 2014年
Molecules. 2015 Apr 24;20(5):7528-57. doi: 10.3390/molecules20057528.
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Synthesis of Fluoren-9-ones and Ladder-Type Oligo-p-phenylene Cores via Pd-Catalyzed Carbonylative Multiple C-C Bond Formation.
通过钯催化的羰基化多碳-碳键形成合成芴-9-酮和梯型低聚对亚苯基核。
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Palladium-catalyzed, ligand-free Suzuki reaction in water using aryl fluorosulfates.钯催化、无配体的水相铃木反应中使用芳基氟硫酸酯。
Org Lett. 2015 Apr 17;17(8):1942-5. doi: 10.1021/acs.orglett.5b00654. Epub 2015 Apr 9.
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A general direct arylation of polyfluoroarenes with heteroaryl and aryl chlorides catalyzed by palladium indolylphosphine complexes.钯吲哚基膦配合物催化的多氟芳烃与杂芳基和芳基氯化物的一般直接芳基化反应。
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