Ruthenium Chloride Catalyzed One-Pot Synthesis of Aldehydes Directly from Benzylic or Primary Alkyl Halides in Aqueous Medium

IF 1.7 4区 化学 Q3 CHEMISTRY, ORGANIC
Synlett Pub Date : 2024-06-21 DOI:10.1055/s-0043-1774928
Kiran Kiran, Senthilkumar Muthaiah
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引用次数: 0

Abstract

We report the first example of an acid- and oxidant-free one-pot conversion of benzylic or primary alkyl halides into aldehydes by using simple ruthenium chloride as the catalyst. The developed synthetic strategy is pot-economical and is also cheap as it uses hexamethylenetetramine as a reagent, employs as little as 0.5 mol% of ruthenium chloride, and efficiently converts the benzylic or primary alkyl halides into aldehydes in aqueous medium. The methodology was also found to be highly selective, as it forms the aldehyde product exclusively without forming possible byproducts, namely amines or carboxylic acids. The methodology is also superior in comparison with the conventional Sommelet and Kornblum oxidation reactions as it avoids the use of excess acid or DMSO, and uses very cheap and ecofriendly hexamethylenetetramine as both the formylating agent and base. The recyclability of the developed catalyst system was also tested, and showed excellent activities for up to three cycles.

Abstract Image

氯化钌催化在水介质中直接从苄基或伯烷基卤化物一步合成醛类化合物
我们首次报道了以简单的氯化钌为催化剂,将苄基或伯烷基卤化物一锅转化为醛的无酸无氧化剂实例。所开发的合成策略既经济又廉价,因为它使用六亚甲基四胺作为试剂,氯化钌的用量仅为 0.5 摩尔%,并能在水介质中有效地将苄基或伯烷基卤化物转化为醛。该方法还具有高度选择性,因为它只形成醛产物,而不会产生可能的副产物,即胺或羧酸。与传统的 Sommelet 和 Kornblum 氧化反应相比,该方法也更胜一筹,因为它避免了使用过量的酸或二甲基亚砜,并使用非常廉价和环保的六亚甲基四胺作为甲酰化剂和碱。此外,还对所开发催化剂系统的可回收性进行了测试,结果表明该催化剂系统在长达三个周期内都具有极佳的活性。
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来源期刊
Synlett
Synlett 化学-有机化学
CiteScore
3.40
自引率
5.00%
发文量
369
审稿时长
1 months
期刊介绍: SYNLETT is an international journal reporting research results and current trends in chemical synthesis in short personalized reviews and preliminary communications. It covers all fields of scientific endeavor that involve organic synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines and offers the possibility to publish scientific primary data.
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