KOtBu-Promoted Halogen-Bond-Assisted Intramolecular C–S Cross-Coupling of o-Iodothioanilides for the Synthesis of 2-Substituted Benzothiazoles,The Journal of Organic Chemistry

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KOtBu-Promoted Halogen-Bond-Assisted Intramolecular C–S Cross-Coupling of o-Iodothioanilides for the Synthesis of 2-Substituted Benzothiazoles
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-10-13 , DOI: 10.1021/acs.joc.1c02023
Anuradha Nandy ₁ , Govindasamy Sekar ₁

Affiliation

An efficacious and mild KO^tBu-promoted intramolecular C–S cross-coupling of ortho-iodothioanilides in conjunction with a catalytic quantity of phenanthroline as an additive has been described for the convenient synthesis of 2-substituted benzothiazoles. The methodology is suitable for attaining a wide variety of 2-alkyl- and 2-aryl-substituted benzothiazoles. Single-crystal XRD, DFT calculations, NMR, and UV studies suggest that halogen bonds between the units of ortho-iodothioanilides may assist in the electron transfer process.

中文翻译：

用于合成 2-取代苯并噻唑的邻碘硫代苯胺的 KOtBu 促进的卤素键辅助分子内 C-S 交叉偶联

已经描述了一种有效且温和的 KO ^t Bu 促进的邻碘硫代苯胺的分子内 C-S 交叉偶联以及催化量的菲咯啉作为添加剂，用于方便地合成 2-取代苯并噻唑。该方法适用于获得多种 2-烷基和 2-芳基取代的苯并噻唑。单晶 XRD、DFT 计算、NMR 和 UV 研究表明，邻碘硫代苯胺单元之间的卤素键可能有助于电子转移过程。

更新日期：2021-11-05

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