TfOH-catalyzed transfer hydrogenation reaction using 1-tetralone as a novel dihydrogen source†

IF 9.3 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Green Chemistry Pub Date : 2024-02-05 DOI:10.1039/d3gc04699k
Yishu Bao , Siyuan Ma , Jin Zhu , Zonghao Dai , Qikun Zhou , Xiuqin Yang , Qingfa Zhou , Fulai Yang
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引用次数: 0

Abstract

An unprecedented TfOH-catalyzed transfer hydrogenation reaction has been developed using 1-tetralone as a novel dihydrogen source. Various alkenes, as well as triphenylmethyl and diphenylmethyl derivatives, have been successfully employed in this transfer hydrogenation reaction, resulting in the formation of various desired products with good yields. Deuterium labeling experiments show that the α-hydrogen of 1-tetralone donated a proton to the alkene, resulting in the formation of a carbenium ion that subsequently captured a hydride originating from the β-hydrogen of 1-tetralone, thereby facilitating a reduction reaction. This study represents a significant advance as it demonstrates the potential of ketones as novel dihydrogen sources for reduction reactions under metal-free conditions.

Abstract Image

Abstract Image

以 1-四氢萘酮为新型二氢源的 TfOH 催化转移加氢反应
以 1-四氢萘酮为新型二氢源,开发出了一种前所未有的 TfOH 催化转移加氢反应。各种烯类以及三苯甲基和二苯甲基衍生物都被成功用于该转移加氢反应,从而以良好的产率生成了各种所需产物。氘标记实验表明,1-四氢萘酮的α-氢向烯烃提供了一个质子,从而形成了一个硒离子,该离子随后捕获了来自 1-四氢萘酮的β-氢的氢化物,从而促进了还原反应。这项研究是一项重大进展,因为它证明了酮作为新型二氢源在无金属条件下进行还原反应的潜力。
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来源期刊
Green Chemistry
Green Chemistry 化学-化学综合
CiteScore
16.10
自引率
7.10%
发文量
677
审稿时长
1.4 months
期刊介绍: Green Chemistry is a journal that provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998), which defines green chemistry as the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry aims to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. The journal welcomes submissions on all aspects of research relating to this endeavor and publishes original and significant cutting-edge research that is likely to be of wide general appeal. For a work to be published, it must present a significant advance in green chemistry, including a comparison with existing methods and a demonstration of advantages over those methods.
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