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通过铃木-宫浦交叉偶联反应合成和功能化具有挑战性取代的芳基双口袋卟啉。

Synthesis and Functionalization of Challenging -Substituted Aryl Bis-pocket Porphyrins Accessed via Suzuki-Miyaura Cross-Coupling.

机构信息

Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, United States.

出版信息

J Org Chem. 2022 Sep 2;87(17):11783-11795. doi: 10.1021/acs.joc.2c01538. Epub 2022 Aug 17.

DOI:10.1021/acs.joc.2c01538
PMID:35976791
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9447288/
Abstract

Herein we report an investigation into the synthesis, metalation, and functionalization of bis-pocket porphyrins using the Suzuki-Miyaura cross-coupling reaction. Steric limitations to accessing bis-pocket porphyrins were overcome by using this Pd-catalyzed C-C-bond-forming strategy to introduce steric bulk macrocyclization: 2,6-dibromo-4-trimethylsilybenzaldehyde was condensed with pyrrole, and a variety of boronic acids were coupled to the resulting porphyrin in up to 95% yield. Furthermore, we show that these porphyrins can be metalated with a variety of metals and sulfonated to create water-soluble bis-pocket porphyrins.

摘要

在这里，我们报告了使用 Suzuki-Miyaura 交叉偶联反应合成、金属化和功能化双口袋卟啉的研究。通过使用这种 Pd 催化的 C-C 键形成策略引入空间位阻大环化，可以克服双口袋卟啉的空间位阻限制：2,6-二溴-4-三甲基甲硅烷基苯甲醛与吡咯缩合，各种硼酸与所得卟啉偶联，产率高达 95%。此外，我们还表明，这些卟啉可以与多种金属配位，并进行磺化以形成水溶性双口袋卟啉。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/22cf/9447288/e9b684e33e6a/jo2c01538_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/22cf/9447288/115f7e4466e2/jo2c01538_0002.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/22cf/9447288/e8e28e34bb8e/jo2c01538_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/22cf/9447288/e9b684e33e6a/jo2c01538_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/22cf/9447288/115f7e4466e2/jo2c01538_0002.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/22cf/9447288/5a1fe0b74616/jo2c01538_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/22cf/9447288/5aaa50197888/jo2c01538_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/22cf/9447288/e8e28e34bb8e/jo2c01538_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/22cf/9447288/e9b684e33e6a/jo2c01538_0007.jpg

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