Thiocyanation of Allylic Alcohols Promoted by Trifluoroacetic Acid-Reference-Cited by-同舟云学术

Thiocyanation of Allylic Alcohols Promoted by Trifluoroacetic Acid

Published:2023-03-30 Issue:16 Volume:26 Page:
ISSN:1434-193X
Container-title:European Journal of Organic Chemistry
language:en
Short-container-title:Eur J Org Chem

Author:

Xia Wen¹,Hu Liangzhen¹,Ma Chenglong¹,Cao Jiaqi¹,Zhang Xiaohui¹,Xiong Yan¹²³^ORCID

Affiliation:

1. School of Chemistry and Chemical Engineering Chongqing University Chongqing 401331 P.R. China

2. Key Laboratory of Pharmaceutical Analysis and Laboratory Medicine Putian University Putian 351100 P. R. China

3. Collaborative Innovation Center for High Value Transformation of Coal Chemical Process By-products School of Chemical and Environmental Engineering Xinjiang Institute of Engineering Xinjiang 830091 P. R. China

Abstract

AbstractA rapid and efficient acid‐promoted strategy to access allylic thiocyanates using allylic alcohols as substrates and easily‐available NH4SCN as the thiocyanate source is presented under metal‐ and oxidant‐free conditions. Through screening of various kinds of acids, organic and strong trifluoroacetic acid (TFA) was found most effective. Testing of substrates showed that the strategy has remarkable functional group tolerance. A possible mechanism is provided, and the gram‐scale experiment demonstrate that this novel protocol has potential industrial application value.

Funder

National Natural Science Foundation of China

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/ejoc.202300148

Reference48 articles.

1. Fasicularin, a novel tricyclic alkaloid from the ascidian Nephteis fasicularis with selective activity against a DNA repair-deficient organism

2. Design, Synthesis, and Biological Evaluation of Aryloxyethyl Thiocyanate Derivatives against Trypanosoma cruzi

3. DNA Damage by Fasicularin

4. Synthesis and Antifungal Activity of Arylthiocyanates

5. Terpenoids with antifouling activity against barnacle larvae from the marine sponge Acanthella cavernosa

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