Photocatalytic/Cu‐Promoted C−H Activations: Visible‐light‐Induced <i>ortho</i>‐Selective Perfluoroalkylation of Benzamides

Chen, Xiang; Tan, Ze; Gui, Qingwen; Hu, Liang; Liu, Jidan; Wu, Jing; Wang, Guangwei

doi:10.1002/chem.201600229

Cited by 45 publications

(21 citation statements)

References 106 publications

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“… [140] For the same reason, however, and because it is not electron‐withdrawing, a methyl group is not a strong amide activator. Because of this, forcing conditions are necessary for the hydrolysis of N ‐methyl activated AQ‐amides (130 °C, 15–72 h) and yields are generally moderate ( 220 – 226 ) [140–146] . Furthermore, base‐labile functional groups may not be tolerated or may require protection ( 226 ).…”

Section: Nucleophilic Cleavage Of the Amide Bondmentioning

confidence: 99%

A Guide to Directing Group Removal: 8‐Aminoquinoline

Fitzgerald

O’Duill

2021

Chemistry A European J

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The use of directing groups allows high levels of selectivity to be achieved in transition metal‐catalyzed transformations. Efficient removal of these auxiliaries after successful functionalization, however, can be very challenging. This review provides a critical overview of strategies used for removal of Daugulis’ 8‐aminoquinoline (2005–2020), one of the most widely used N,N‐bidentate directing groups. The limitations of these strategies are discussed and alternative approaches are suggested for challenging substrates. Our aim is to provide a comprehensive end‐users’ guide for chemists in academia and industry who want to harness the synthetic power of directing groups—and be able to remove them from their final products.

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Section: Nucleophilic Cleavage Of the Amide Bondmentioning

confidence: 99%

A Guide to Directing Group Removal: 8‐Aminoquinoline

Fitzgerald

O’Duill

2021

Chemistry A European J

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“…In 2016, Tan, Wang and co-workers developed a methodology allowing the ortho-perfluoroalkylation of benzamides. This reaction photoinduced by visible light was promoted by copper and used the bidentate 8-aminoquinoline moiety as the DG (Figure 33) [98]. Remarkably, eosin Y, a cheap organic photocatalyst, enhanced the generation of perfluoroalkyl radicals from the corresponding alkyl iodides but a stoichiometric amount of a simple copper salt, acting as both, the catalyst for C-H activation and the oxidizing agent, was also required.…”

Section: Cu-catalyzed Transformationsmentioning

confidence: 99%

When metal-catalyzed C–H functionalization meets visible-light photocatalysis

Guillemard¹,

Wencel‐Delord²

2020

Beilstein J. Org. Chem.

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While aiming at sustainable organic synthesis, over the last decade particular attention has been focused on two modern fields, C–H bond activation, and visible-light-induced photocatalysis. Couplings through C–H bond activation involve the use of non-prefunctionalized substrates that are directly converted into more complex molecules, without the need of a previous functionalization, thus considerably reduce waste generation and a number of synthetic steps. In parallel, transformations involving photoredox catalysis promote radical reactions in the absence of radical initiators. They are conducted under particularly mild conditions while using the visible light as a cheap and economic energy source. In this way, these strategies follow the requirements of environment-friendly chemistry. Regarding intrinsic advantages as well as the complementary mode of action of the two catalytic transformations previously introduced, their merging in a synergistic dual catalytic system is extremely appealing. In that perspective, the scope of this review aims to present innovative reactions combining C–H activation and visible-light induced photocatalysis.

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“…The first reports on the trifluoromethylation of anilide derivatives photocatalyzed by eosin Yw ith Cu II salts and Cs 2 CO 3 have been informed by Chen, Tan, Wang and co-workers. [43] An ew example on eosin Y-photocatalyzed trifluoromethylation of arenes is that reported by Tian, An, Li, and co-workers [44] who studied the trifluoromethylation of anilide derivatives in the ortho-CÀHp osition by using CF 3 SO 2 Na towards the synthesis of trifluoromethyl lactams. The scope of the transformation is succinctly illustrated in Scheme 2.…”

Section: New Examples Of Organo-photocatalyzed Trifluoromethylations mentioning

confidence: 99%

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

Barata‐Vallejo

Postigo

2020

Chemistry A European J

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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 CF3 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.

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Photocatalytic/Cu‐Promoted C−H Activations: Visible‐light‐Induced ortho‐Selective Perfluoroalkylation of Benzamides

Cited by 45 publications

References 106 publications

A Guide to Directing Group Removal: 8‐Aminoquinoline

A Guide to Directing Group Removal: 8‐Aminoquinoline

When metal-catalyzed C–H functionalization meets visible-light photocatalysis

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

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