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新型可见光引发的碳碳多重键与(杂)芳环化合物的三氟甲基化反应。

New Visible-Light-Triggered Photocatalytic Trifluoromethylation Reactions of Carbon-Carbon Multiple Bonds and (Hetero)Aromatic Compounds.

机构信息

Department of Organic Chemistry, Universidad de Buenos Aires, Facultad de Farmacia y Bioquímica, Junin 954 CP, 1113 Buenos, Aires, Argentina.

ISOF, Consiglio Nazionale delle Ricerche, Via P. Gobetti 101, 40129, Bologna, Italy.

出版信息

Chemistry. 2020 Sep 1;26(49):11065-11084. doi: 10.1002/chem.202000856. Epub 2020 Jul 8.

Abstract

Visible-light-photocatalyzed methods employed in synthetic transformations present attractive properties such as environmentally friendly, safety, availability and excellent functional group tolerance. In this regard, research on the visible-light photocatalytic incorporation of the trifluoromethyl CF moiety into organic substrates, in particular, has contributed to a clear evolution of the field of photocatalysis. Although this particular area is constantly evolving and has been reviewed, the last five years have experienced an outburst of seminal and significant photocatalytic trifluoromethylation examples that are leading the way and opening new synthetic avenues. Recent review articles on Ru- and Ir-based photocatalytic trifluoromethylation reactions have borne witness of this evolution. Although this account will show the new Ru- and Ir-based photocatalytic trifluoromethylations, Sections 2 and 3 will also illustrate other photocatalytic systems, such as organic dyes, organic semiconductors and newly-developed all-organic photocatalysts. All the known and reviewed strategies for photocatalytic trifluoromethylation reactions of olefins and (hetero)aromatic compounds will not be discussed but will be summarized in two figures (Figures 4 and 5), and new examples (2015-present) will be presented and discussed.

摘要

可见光催化合成转化方法具有环境友好、安全、易得和对官能团容忍性好等优点。在这方面,可见光催化将三氟甲基 CF 基团引入有机底物的研究极大地推动了光催化领域的发展。尽管这一特定领域在不断发展并已经被综述,但在过去五年中,具有开创性和重要意义的光催化三氟甲基化实例如雨后春笋般涌现,引领着新的合成途径。最近关于 Ru 和 Ir 基光催化三氟甲基化反应的综述文章见证了这一演变。虽然本综述将展示新的 Ru 和 Ir 基光催化三氟甲基化,但第 2 节和第 3 节还将介绍其他光催化体系,如有机染料、有机半导体和新开发的全有机光催化剂。所有已知的和综述的烯烃和(杂)芳环化合物的光催化三氟甲基化反应策略将不进行讨论,而将在两个图(图 4 和图 5)中进行总结,并将呈现和讨论新的实例(2015 年至今)。

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