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苯基碘双(三氟乙酸酯)作为一种可持续试剂:探索其在有机合成中的意义。

Phenyliodine bis(trifluoroacetate) as a sustainable reagent: exploring its significance in organic synthesis.

作者信息

Kumar Sumit, Arora Aditi, Singh Sunil K, Kumar Rajesh, Shankar Bhawani, Singh Brajendra K

机构信息

Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi-110007, India.

Department of Chemistry, Kirori Mal College, University of Delhi, Delhi-110007, India.

出版信息

Org Biomol Chem. 2024 Apr 24;22(16):3109-3185. doi: 10.1039/d3ob01964k.

DOI:10.1039/d3ob01964k
PMID:38529599
Abstract

Iodine-containing molecules, especially hypervalent iodine compounds, have gained significant attention in organic synthesis. They are valuable and sustainable reagents, leading to a remarkable surge in their use for chemical transformations. One such hypervalent iodine compound, phenyliodine bis(trifluoroacetate)/bis(trifluoroacetoxy)iodobenzene, commonly referred to as PIFA, has emerged as a prominent candidate due to its attributes of facile manipulation, moderate reactivity, low toxicity, and ready availability. PIFA presents an auspicious prospect as a substitute for costly organometallic catalysts and environmentally hazardous oxidants containing heavy metals. PIFA exhibits remarkable catalytic activity, facilitating an array of consequential organic reactions, including sulfenylation, alkylarylation, oxidative coupling, cascade reactions, amination, amidation, ring-rearrangement, carboxylation, and numerous others. Over the past decade, the application of PIFA in synthetic chemistry has witnessed substantial growth, necessitating an updated exploration of this field. In this discourse, we present a concise overview of PIFA's applications as a 'green' reagent in the domain of synthetic organic chemistry. A primary objective of this article is to bring to the forefront the scientific community's awareness of the merits associated with adopting PIFA as an environmentally conscientious alternative to heavy metals.

摘要

含碘分子,尤其是高价碘化合物,在有机合成中受到了广泛关注。它们是有价值且可持续的试剂,其在化学转化中的应用显著增加。一种这样的高价碘化合物,苯基碘双(三氟乙酸酯)/双(三氟乙酰氧基)碘苯,通常称为PIFA,因其易于操作、反应活性适中、毒性低且易于获得等特性,已成为一个突出的候选物。PIFA作为昂贵的有机金属催化剂和含有重金属的环境有害氧化剂的替代品,展现出良好的前景。PIFA表现出显著的催化活性,能促进一系列重要的有机反应,包括亚磺酰化、烷基芳基化、氧化偶联、串联反应、胺化、酰胺化、环重排、羧化以及许多其他反应。在过去十年中,PIFA在合成化学中的应用有了显著增长,因此有必要对该领域进行更新的探索。在本文中,我们简要概述了PIFA作为“绿色”试剂在合成有机化学领域中的应用。本文的一个主要目的是让科学界更加关注采用PIFA作为重金属的环保替代品所具有的优点。

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Phenyliodine bis(trifluoroacetate) as a sustainable reagent: exploring its significance in organic synthesis.苯基碘双(三氟乙酸酯)作为一种可持续试剂:探索其在有机合成中的意义。
Org Biomol Chem. 2024 Apr 24;22(16):3109-3185. doi: 10.1039/d3ob01964k.
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