CF(3)-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry.

CF(3)-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry.
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DOI:
10.3762/bjoc.17.32
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发表时间:
2021
影响因子:
2.7
通讯作者:
Thibaudeau S
Thibaudeau S
中科院分区:
化学4区
文献类型:
--
作者:
Fernandes AJ;Panossian A;Michelet B;Martin-Mingot A;Leroux FR;Thibaudeau S

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“这种‘离子’的异常不稳定性解释了有机反应的许多特殊性”-- Franck C. Whitmore(1932).惠特莫尔的这一说法是在碳正离子开始被认为是反应中间体的时期提出的。90年后,从著名有机化学家的贡献中获得的强大知识,碳正离子是非常知名的反应中间体。其中,不稳定的碳阳离子-碳阳离子取代吸电子基团-然而,仍然注定是短暂的物种,有时被认为是外来的。其中,CF 3-取代的碳正离子,经常被认为是参与合成转化,但很少被认为是负担得起的合成目的的中间体,长期以来一直在研究。本文综述了最近和过去的报告,重点是他们的研究和潜力,在现代合成转化。
“The extraordinary instability of such an “ion” accounts for many of the peculiarities of organic reactions” – Franck C. Whitmore (1932). This statement from Whitmore came in a period where carbocations began to be considered as intermediates in reactions. Ninety years later, pointing at the strong knowledge acquired from the contributions of famous organic chemists, carbocations are very well known reaction intermediates. Among them, destabilized carbocations – carbocations substituted with electron-withdrawing groups – are, however, still predestined to be transient species and sometimes considered as exotic ones. Among them, the CF3-substituted carbocations, frequently suggested to be involved in synthetic transformations but rarely considered as affordable intermediates for synthetic purposes, have long been investigated. This review highlights recent and past reports focusing on their study and potential in modern synthetic transformations.
DOI: 10.1021/acs.chemrev.8b00083
发表时间: 2018-09-12
期刊: Chemical reviews
影响因子: 62.1
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