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区域选择性亲电芳香硼化反应作为一种合成位阻苯并噻二唑荧光团的方法。

Regioselective electrophilic aromatic borylation as a method for synthesising sterically hindered benzothiadiazole fluorophores.

作者信息

Taylor Dominic, Malcomson Thomas, Zhakeyev Adilet, Rosair Georgina M, Paterson Martin J, Marques-Hueso Jose, Dalgarno Scott J, Vilela Filipe

机构信息

Institute of Chemical Sciences, School of Engineering and Physical Science, Heriot-Watt University Riccarton Edinburgh EH14 4AS UK

Department of Chemistry, Lancaster University Lancaster LA1 4YB UK.

出版信息

RSC Adv. 2023 Feb 16;13(9):5826-5832. doi: 10.1039/d2ra08319a. eCollection 2023 Feb 14.

DOI:10.1039/d2ra08319a
PMID:36846398
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9951066/
Abstract

Regioselective stepwise phenylation of 4,7-diarylbenzo[][1,2,5]thiadiazole fluorophores has been achieved through a facile one-pot, three-step synthetic strategy involving sequential borylation, hydroxydechlorination and Suzuki-Miyaura cross-coupling reactions. Crucial to the selectivity was the use of BCl to regioselectively install a boronic acid group in the -position of only one of the diaryl groups. The subsequent introduction of -phenyl groups through Suzuki-Miyaura cross-coupling gave rise to twisted structures with hindered intramolecular rotation, providing a structural lever with which the fluorophore absorption and emission properties could be adjusted.

摘要

通过一种简便的一锅三步骤合成策略，实现了4,7 - 二芳基苯并[][1,2,5]噻二唑荧光团的区域选择性逐步苯基化，该策略涉及连续的硼化、羟基脱氯和铃木 - 宫浦交叉偶联反应。选择性的关键在于使用BCl在仅一个二芳基的α位区域选择性地安装硼酸基团。随后通过铃木 - 宫浦交叉偶联引入对苯基，产生了具有受阻分子内旋转的扭曲结构，提供了一种可调节荧光团吸收和发射特性的结构手段。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7c8/9951066/162a3de841b7/d2ra08319a-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7c8/9951066/043bdbbefa8e/d2ra08319a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7c8/9951066/2f1fb6e3d030/d2ra08319a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7c8/9951066/32e44a96c2bb/d2ra08319a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7c8/9951066/92d91449f7fd/d2ra08319a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7c8/9951066/5cbed1ecdc46/d2ra08319a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7c8/9951066/162a3de841b7/d2ra08319a-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7c8/9951066/043bdbbefa8e/d2ra08319a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7c8/9951066/2f1fb6e3d030/d2ra08319a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7c8/9951066/32e44a96c2bb/d2ra08319a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7c8/9951066/92d91449f7fd/d2ra08319a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7c8/9951066/5cbed1ecdc46/d2ra08319a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7c8/9951066/162a3de841b7/d2ra08319a-f4.jpg

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