Aqueous microwave assisted novel synthesis of isothiocyanates by amine catalyzed thionation of isocyanides with Lawesson's reagent

IF 2.1 3区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Sulfur Chemistry Pub Date : 2023-06-01 DOI:10.1080/17415993.2022.2164196

Sodeeq Aderotimi Salami , Vincent J. Smith , Rui W.M. Krause

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引用次数: 1

Abstract

A green and sustainable chemistry approach for organic synthesis is described here, which involves microwave exposure of reactants in the presence of water. A general, practical, and highly efficient protocol for the preparation of a broad range of functionalized isothiocyanates has been developed from their corresponding isocyanides using Lawesson's reagent and catalytic amount of amine bases, particularly triethylamine under microwave irradiation conditions. As opposed to established approaches that employ toxic or volatile electrophilic liquids (thiophosgene, its derivatives, or CS₂). In addition, these compounds were synthesized also by conventional heating procedures for comparison. Comparison between conventional and microwave-assisted synthesis was carried out by comparing total reaction time and percentage yield. The results suggest that microwave-assisted syntheses lead to higher yields within very short reaction times.

From isocyanides to isothiocyanates using Lawesson’s reagent in the presence of triethylamine under conventional and microwave heating conditions.

查看原文本刊更多论文

用Lawesson试剂胺催化硫代异氰酸酯合成异硫氰酸酯

本文介绍了一种用于有机合成的绿色和可持续的化学方法，该方法涉及反应物在水存在下的微波暴露。在微波辐射条件下，使用Lawesson试剂和催化量的胺碱，特别是三乙胺，从其相应的异氰酸酯出发，开发了一种制备广泛功能化异硫氰酸酯的通用、实用和高效方案。与使用有毒或挥发性亲电液体（硫光气、其衍生物或CS2）的既定方法相反。此外，还通过常规加热程序合成了这些化合物以进行比较。通过比较总反应时间和产率百分比，对常规合成和微波辅助合成进行了比较。结果表明，微波辅助合成在很短的反应时间内产生更高的产率。在三乙胺存在下，在常规和微波加热条件下，使用Lawesson试剂从异氰酸酯到异硫氰酸酯。图形摘要

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

Journal of Sulfur Chemistry CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

4.10

自引率

9.10%

发文量

审稿时长

6-12 weeks

期刊介绍： The Journal of Sulfur Chemistry is an international journal for the dissemination of scientific results in the rapidly expanding realm of sulfur chemistry. The journal publishes high quality reviews, full papers and communications in the following areas: organic and inorganic chemistry, industrial chemistry, materials and polymer chemistry, biological chemistry and interdisciplinary studies directly related to sulfur science. Papers outlining theoretical, physical, mechanistic or synthetic studies pertaining to sulfur chemistry are welcome. Hence the target audience is made up of academic and industrial chemists with peripheral or focused interests in sulfur chemistry. Manuscripts that truly define the aims of the journal include, but are not limited to, those that offer: a) innovative use of sulfur reagents; b) new synthetic approaches to sulfur-containing biomolecules, materials or organic and organometallic compounds; c) theoretical and physical studies that facilitate the understanding of sulfur structure, bonding or reactivity; d) catalytic, selective, synthetically useful or noteworthy transformations of sulfur containing molecules; e) industrial applications of sulfur chemistry; f) unique sulfur atom or molecule involvement in interfacial phenomena; g) descriptions of solid phase or combinatorial methods involving sulfur containing substrates. Submissions pertaining to related atoms such as selenium and tellurium are also welcome. Articles offering routine heterocycle formation through established reactions of sulfur containing substrates are outside the scope of the journal.