α-(N-烷基-N-庚烯)-α-重氮乙酸酯：一类新型 "鎓 "重氮化合物的合成和反应活性

IF 2.7 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2024-09-11 DOI:10.1039/d4ob01056f

Ya-Xi Li , Quan-Yun Liu , Yi Zhang , Miao-Miao Liu , Xiaoqian Liu , Mei-Hua Shen , Fang-Ming Wang , Hua-Dong Xu

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引用次数: 0

摘要

用烷基化试剂处理α-(N-庚芳基)-α-重氮乙酸烷基酯，可得到重氮乙酸 N-庚烯盐。这些新型 "鎓 "重氮化合物大多为黄色固体，具有更高的热稳定性和酸稳定性。在温和的条件下，它们的四氟硼酸盐会发生铑催化的 [2 + 1] 和 Doyle-Kirmse 反应，这表明 N-季铵化是消除 N-配位引起的催化剂毒性的有效方法。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

α-(N-Alkyl-N-heteroarenium)-α-diazoacetates: synthesis and reactivity of a novel class of ‘onium’ diazo compounds†

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α-(N-Alkyl-N-heteroarenium)-α-diazoacetates: synthesis and reactivity of a novel class of ‘onium’ diazo compounds†

Treatment of alkyl α-(N-heteroaryl)-α-diazoacetates with alkylating reagents affords diazoacetate N-heteroarenium salts. These novel ‘onium’ diazo compounds are mostly yellow solids, displaying increased thermal and acid stability. Their tetrafluoroborates undergo rhodium catalyzed [2 + 1] and Doyle–Kirmse reactions under mild conditions, suggesting the N-quaternization an effective means of elimination of N-coordination caused catalyst toxicity.

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来源期刊

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.