Rapid Access to Highly Functionalized Thietanes via Electrophilic Thietanylation under Metal-Free Conditions

IF 4.5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2026-09-23 DOI:10.1039/d6qo01107a

NEHA RAJENDRA THAKAR,Pujan Sasmal,Natish .,Ravi Kumar

引用次数: 0

Abstract

Four-membered heterocycles have profound applications in modern drug discovery. While significant attention has been devoted to oxetane and azetidine functionalization, their sulfur counterpart, thietane, remains underdeveloped due to several synthetic challenges. Herein, we disclose the expedient functionalization of thietane trichloroacetimidates (TTAs) under metal-free conditions to form 3,3-disubstituted thietanes. The reaction accommodates diverse nucleophiles bearing nitrogen, carbon, and sulfur and can be easily scaled up to the gram scale. Mechanistic studies revealed the generated carbocation either underwent a ring-opening or was trapped by HFIP to form a stable HFIP adduct.

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在无金属条件下通过亲电乙烷化快速获得高功能化的乙烷

四元杂环化合物在现代药物发现中有着广泛的应用。虽然人们对氧乙烷和氮杂啶的功能化已经投入了大量的关注，但由于一些合成方面的挑战，它们的硫对应物硫烷仍然不发达。在此，我们公开了在无金属条件下三氯乙酸乙酯（TTAs）的便利官能化，以形成3,3-二取代的乙烷。该反应可容纳多种含氮、碳和硫的亲核试剂，并且可以很容易地按比例放大到克级。机理研究表明，生成的碳正离子要么发生开环，要么被HFIP捕获，形成稳定的HFIP加合物。

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.