在芳烃中选择性引入全氟叔丁基(PFtB,CF3基团的更大类似物)一直是人们追求的目标,但仍然是一项艰巨的任务。
该文中,研究人员报告了实现芳香族全氟叔丁基化的第一个通用合成方案。成功的关键是确定PFtB苯基砜作为PFtB阴离子的新来源,它以高度区域选择性的方式与芳基反应,以高产率提供全氟叔丁基化芳烃。通过制备具有非凡分辨能力的灵敏的19F标记的NMR探针证明了该方法的应用。
附:英文原文
Title: Regioselective Aromatic Perfluoro-tert-butylation Using Perfluoro-tert-butyl Phenyl Sulfone and Arynes
Author: Zhiqiang Wei, Lixian Wen, Kaidi Zhu, Qian Wang, Yanchuan Zhao, Jinbo Hu
Issue&Volume: November 22, 2022
Abstract: The selective introduction of perfluoro-tert-butyl group (PFtB, the bulkier analogue of CF3 group) into arenes has long been sought after but remains a formidable task. We herein report the first general synthetic protocol to realize aromatic perfluoro-tert-butylation. The key to the success is the identification of PFtB phenyl sulfone as a new source of PFtB anion, which reacts with arynes in a highly regioselective manner to afford perfluoro-tert-butylated arenes in high yields. The application of the method is demonstrated by the preparation of sensitive 19F-labeled NMR probes with an extraordinary resolving ability.
DOI: 10.1021/jacs.2c10479
Source: https://pubs.acs.org/doi/10.1021/jacs.2c10479
JACS:《美国化学会志》,创刊于1879年。隶属于美国化学会,最新IF:14.612
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