A Remarkably Efficient Phase-Transfer Catalyzed Amination of α-Bromo-α, β-Unsaturated Ketones in Water

IF 1.1 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Heteroatom Chemistry Pub Date : 2021-01-04 DOI:10.1155/2021/6616458

Alemayehu Mekonnen, A. Tesfaye

引用次数: 1

Abstract

Tandem conjugate addition–alkylation reaction of various amines with α-bromo-α, β-unsaturated ketones resulted in near-quantitative conversions into the corresponding aziridines when the reaction was carried out in the presence of 10 mol% of phase-transfer, PT catalysts in water. Some chiral quaternary ammonium salts derived from Cinchona alkaloids were investigated as water-stable PT catalysts. The scope and limitations of the reaction have also been investigated. The catalytic performances were significantly improved in comparison with the corresponding ordinary quaternary ammonium salt catalysts, and excellent yields (81%–96%) were obtained. Although an increase in the rate of aziridination has been accomplished, no stereoselectivity was observed. The positive values of the protocol have been confirmed.

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相转移催化α-溴-α， β-不饱和酮在水中的高效胺化反应

各种胺与α-溴-α，β-不饱和酮的串联共轭加成-烷基化反应在10 相转移的mol%，PT催化剂在水中。以金鸡纳生物碱为原料，研究了几种手性季铵盐作为水稳性PT催化剂。还对反应的范围和局限性进行了研究。与相应的普通季铵盐催化剂相比，该催化剂的催化性能显著提高，获得了优异的产率（81%–96%）。尽管已经实现了氮丙啶化速率的增加，但没有观察到立体选择性。该方案的正值已得到确认。

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

Heteroatom Chemistry 化学-化学综合

CiteScore

1.20

自引率

0.00%

发文量

审稿时长

6 months

期刊介绍： Heteroatom Chemistry brings together a broad, interdisciplinary group of chemists who work with compounds containing main-group elements of groups 13 through 17 of the Periodic Table, and certain other related elements. The fundamental reactivity under investigation should, in all cases, be concentrated about the heteroatoms. It does not matter whether the compounds being studied are acyclic or cyclic; saturated or unsaturated; monomeric, polymeric or solid state in nature; inorganic, organic, or naturally occurring, so long as the heteroatom is playing an essential role. Computational, experimental, and combined studies are equally welcome. Subject areas include (but are by no means limited to): -Reactivity about heteroatoms for accessing new products or synthetic pathways -Unusual valency main-group element compounds and their properties -Highly strained (e.g. bridged) main-group element compounds and their properties -Photochemical or thermal cleavage of heteroatom bonds and the resulting reactivity -Uncommon and structurally interesting heteroatom-containing species (including those containing multiple bonds and catenation) -Stereochemistry of compounds due to the presence of heteroatoms -Neighboring group effects of heteroatoms on the properties of compounds -Main-group element compounds as analogues of transition metal compounds -Variations and new results from established and named reactions (including Wittig, Kabachnik–Fields, Pudovik, Arbuzov, Hirao, and Mitsunobu) -Catalysis and green syntheses enabled by heteroatoms and their chemistry -Applications of compounds where the heteroatom plays a critical role. In addition to original research articles on heteroatom chemistry, the journal welcomes focused review articles that examine the state of the art, identify emerging trends, and suggest future directions for developing fields.