Electrochemical phosphorothiolation and 1,4-S → C phospho-Fries rearrangement: controlled access to phosphorothiolated and mercapto-phosphono substituted indolizines†

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2023-09-11 DOI:10.1039/D3QO01042B

Xiang Liu, Wenxuan Jiang, Changfeng Huang, Shaohong Ma, Qiong Wang and Hua Cao

引用次数: 0

Abstract

An unprecedented electrochemically regioselective C–H phosphorothiolation and S- to C-[1,4] phosphoryl migration involving indolizines, elemental sulfur, and H-phosphonates in an undivided cell has been developed. This strategy utilizes elemental sulfur as an odorless sulfur source, providing a new avenue for the formation of C(sp²)–S–P bonds under sustainable conditions. Various phosphorothiolated and mercapto-phosphono substituted indolizines were obtained via controllable electrochemical phosphorothiolation and a 1,4-S → C phospho-Fries rearrangement. Additionally, this is the first example of successive electrochemical phosphorothiolation and a 1,4-S → C phospho-Fries rearrangement.

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电化学磷化与1,4-S→ C磷酸-Fries重排：对硫代磷酸化和巯基膦酰基取代的中氮茚的控制获取†

在一个不可分割的细胞中，开发了一种前所未有的电化学区域选择性C–H硫代磷酸化和S至C-[1,4]磷酰基迁移，涉及中氮茚、元素硫和H-膦酸盐。该策略利用元素硫作为无臭硫源，为在可持续条件下形成C（sp2）–S–P键提供了一条新途径。通过可控的电化学硫代磷酸化和1，4-S，得到了各种硫代和巯基膦取代的中氮茚→ C磷酸-Frees重排。此外，这是连续电化学硫代磷酸化和1,4-S的第一个例子→ C磷酸-Frees重排。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.