University of Sherbrooke , Department of Chemistry, Centre in Green Chemistry and Catalysis, 2500 boul. de l'Université, Sherbrooke, Québec J1K 2R1, Canada.
Org Lett. 2017 Dec 1;19(23):6420-6423. doi: 10.1021/acs.orglett.7b03307. Epub 2017 Nov 16.
The synthesis of a new family of iodonium zwitterions, in which the formal anion is a trifluoroborate moiety, is reported. These reagents present very good stability and have high resistance toward benzyne formation. Their structures were confirmed by X-ray crystallographic analysis and were further investigated using DFT calculations. QTAIM analysis supports an ionic, noncovalent, I···BF interaction, in accordance with a true zwitterionic nature. Preliminary results of synthetic applications, the arylation of phenolates and trifluoroborate group functionalization, are reported.
报告了一种新型碘鎓两性离子的合成方法，其中的形式阴离子是三氟硼酸根部分。这些试剂具有非常好的稳定性，对苯炔的形成具有很高的抗性。它们的结构通过 X 射线晶体学分析得到证实，并进一步通过 DFT 计算进行了研究。QTAIM 分析支持离子型、非共价的 I···BF 相互作用，符合真正的两性离子性质。报告了它们在合成应用中的初步结果，包括酚盐的芳基化和三氟硼酸酯基团的官能化。
