Transition-metal-free direct perfluoroalkylation of quinoline amides at C5 position through radical cross-coupling under mild conditions

Zhang, Pengfei; Li, Qiao; Ying, Beibei; Zhu, Xiaolei; Shen, Chao; Zhang, Pengfei

doi:10.1039/c6qo00655h

Cited by 54 publications

(20 citation statements)

References 87 publications

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“…To the best of our knowledge, transition‐metal‐free direct C−H trifluoromethylation of nonprefunctionalized heterocyles using TMSCF 3 as trifluoromethyl agent near room temperature is less reported ,. In addition, compared to trifluoromethylation, efficient and general methods for direct C−H perfluoroalkylation of nonprefunctionalized heterocyles with TMSC 2 F 5 or TMSC 3 F 7 are comparatively rare ,,,. Thus, expanding the application of TMSC n F 2n+1 (n=1, 2, 3) in the fluorination of organic compound with higher atom‐efficient as well as getting the useful fluoroalkylated molecules is still challenging.…”

Section: Methodsmentioning

confidence: 99%

Transition‐Metal‐Free Direct Trifluoromethylation and Perfluoroalkylation of Imidazopyridines under Mild Conditions

Han

Gao

et al. 2019

Adv Synth Catal

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The first transition-metal-free method for direct CÀH trifluoromethylation of imidazo[1,2a]pyridine derivatives with readily available Ruppert-Prakash reagent TMSCF 3 under mild conditions was described. Moreover, this method could be applied to direct CÀH perfluoroalkylation of imidazopyridines, affording a series of novel perfluoroalkylated products in moderate to good yields. Notable advantages of this protocol include easy operation, high-efficiency and wide substrate scope.

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Section: Methodsmentioning

confidence: 99%

Transition‐Metal‐Free Direct Trifluoromethylation and Perfluoroalkylation of Imidazopyridines under Mild Conditions

Han

Gao

et al. 2019

Adv Synth Catal

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“…In 2017, Zhang's research group demonstrated PIDA-mediated C-H perfluoroalkylation of 8-aminoquinoline amides 369 to yield perfluoroalkylated quinolones 371 (Scheme 100). 130 Reaction scope was administered by using different perfluoroalkyl sources 370 such as TMSC2F5, TMSn-C3F7 and TMSCF3. Based on the various control experiments, it was confirmed that reaction proceeds via single electron transfer mechanism.…”

Section: Alkylation/alkynylation Of Heterocylesmentioning

confidence: 99%

Hypervalent iodine-mediated synthesis and late-stage functionalization of heterocycles

Shetgaonkar¹,

Singh²

2021

Arkivoc

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Hypervalent iodine chemistry has witnessed exponential growth in organic synthesis in recent times. Because of the electrophilic and good-leaving nature of hypervalent iodine reagents, they react with different nucleophiles in various synthetic transformations such as rearrangements, α-functionalization of carbonyl compounds, alkene difunctionalization and oxidation reactions. Importantly, the application of hypervalent iodine reagents in the construction of heterocycles is of great interest and has been well studied over the years. This review article highlights the recent developments accomplished by hypervalent iodine reagents in the synthesis and functionalization of heterocyclic compounds.

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“…In 2017, Zhang and co‐workers reported a simple and effective method for the preparation of 5‐perfluoroalkylquinoline amides involving the C‐5 selective perfluoroalkylation of quinoline amides via coupling of 8‐aminoquinoline amides with perfluoroalkyl compounds (Scheme ) . The reaction is characterized by transition metal‐free catalysis, mild conditions (room temperature), short reaction times and high yields, and tolerance of various functional groups.…”

Section: Para‐c–h Functionalization Of Aromatic Amidesmentioning

confidence: 99%

C–H Functionalization of Aromatic Amides

et al. 2020

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Since the beginning of the 21st century, significant progress has been made in transition metal‐catalyzed C–H functionalization of aromatic amides. The achievements in this field have mainly focused on ortho (proximal) functionalization, there have been far fewer reports on remote C–H functionalization, and para‐ and meta‐selective functionalizations remain a major challenge. Interestingly, there are few related comments in this field. In a few published cases, the scope of the report is relatively narrow, either to comment on the functionalization of a specific directing group or to summarize the functionalization of a specific reaction site. Herein, for the first time, we have comprehensively summarized the C–H functionalization of aromatic amides. This review is divided into three parts: ortho‐, para‐ and meta‐C–H functionalization of aromatic amides, and is subdivided according to the type of catalyst. The directing groups, reaction types, conditions, mechanism and applications of the corresponding reactions are discussed in detail.

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Transition-metal-free direct perfluoroalkylation of quinoline amides at C5 position through radical cross-coupling under mild conditions

Abstract: A simple low-energy and efficient method is established for the synthesis of C5-selective perfluoroalkylation quinolines in the absence of any transition metal catalysts.

Cited by 54 publications

References 87 publications

Transition‐Metal‐Free Direct Trifluoromethylation and Perfluoroalkylation of Imidazopyridines under Mild Conditions

Transition‐Metal‐Free Direct Trifluoromethylation and Perfluoroalkylation of Imidazopyridines under Mild Conditions

Hypervalent iodine-mediated synthesis and late-stage functionalization of heterocycles

C–H Functionalization of Aromatic Amides

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