Bi（III）催化Newman-Kwart重排合成s -杂芳基硫氨基甲酸酯

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-02-20 DOI:10.1021/acs.joc.4c0272810.1021/acs.joc.4c02728

Yuma Okuda, Keita Yamazaki and Tetsuhiro Nemoto*,

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引用次数: 0

摘要

Newman-Kwart重排法（NKR）是由o -芳基硫氨基甲酸酯合成s -芳基硫氨基甲酸酯的有效方法。然而，需要苛刻的温度条件，导致底物降解和副反应。此外，使用杂芳香族底物的反应相当罕见。本文报道了Bi(OTf)3在常温条件下使用杂芳香族底物催化NKR。该反应不仅扩展到氮杂芳烃底物，而且扩展到噻吩底物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Bi(III)-Catalyzed Newman–Kwart Rearrangement for Synthesizing S-Heteroaryl Thiocarbamates

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Bi(III)-Catalyzed Newman–Kwart Rearrangement for Synthesizing S-Heteroaryl Thiocarbamates

Newman–Kwart rearrangement (NKR) is a useful method for synthesizing S-aryl thiocarbamates from O-aryl thiocarbamates. Harsh temperature conditions are required, however, leading to substrate degradation and side reactions. Moreover, reactions using heteroaromatic substrates are quite rare. Herein, we report Bi(OTf)₃-catalyzed NKR using heteroaromatic substrates under ambient temperature conditions. The reaction extended to not only aza-arene substrates but also thiophene substrates.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.