<i>N</i>‐Trifluoromethyl Hydrazines, Indoles and Their Derivatives

Bouayad‐Gervais, Samir; Scattolin, Thomas; Schoenebeck, Franziska

doi:10.1002/anie.202004321

Cited by 40 publications

(17 citation statements)

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“…However, these synthetic strategies fail to deliver the corresponding N -CF 3 alkynamides. With the goal to develop the first synthetic access to these promising motifs and hence also potentially unlock access to alternative potent N -CF 3 derivatives, , we set out to develop a catalytic route to convert N -CF 3 carbamoyl fluorides to the corresponding alkynamides (Figure D).…”

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confidence: 99%

Synthesis of N-CF₃ Alkynamides and Derivatives Enabled by Ni-Catalyzed Alkynylation of N-CF₃ Carbamoyl Fluorides

2021

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The expansion of chemical space associated with ubiquitous motifs is key to unleash new properties and functions. In this context, alkynamides, prevalent in numerous drugs and materials, represent an untapped resource. We herein report the first synthetic access to N-trifluoromethyl alkynamides. Our strategy relies on a mild and operationally simple Ni-catalyzed coupling of N-CF 3 carbamoyl fluorides with alkynyl silanes. The synthesized N-CF 3 alkynamides proved to be highly robust and readily functioned as a platform to unlock access to valuable derivatives, such as N-CF 3 decorated alkenyl amides, oxindoles, or quinolones, all of which were inaccessible to date.

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confidence: 99%

Synthesis of N-CF₃ Alkynamides and Derivatives Enabled by Ni-Catalyzed Alkynylation of N-CF₃ Carbamoyl Fluorides

2021

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“…In 2019, Schoenebeck et al reported straight access to N -CF 3 amides, carbamates, thiocarbamates or ureas via N -CF 3 carbomoyl building blocks 61 [ 88 ]. After that, the same group developed the transformation of the building blocks and generated non-cyclic or heterocyclic N -CF 3 compounds as shown in Scheme 15 [ 89 , 90 , 91 , 92 ]. Additionally, antihistamine derivative oxatomide analogue 64a could be generated in 62% in two steps by N-H functionalization of 64 .…”

Section: Five-membered Heterocyclesmentioning

confidence: 99%

A Brief Review on the Synthesis of the N-CF3 Motif in Heterocycles

et al. 2023

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The trifluoromethyl group is widely recognized for its significant role in the fields of medicinal chemistry and material science due to its unique electronic and steric properties that can alter various physiochemical properties of the parent molecule, such as lipophilicity, acidity, and hydrogen bonding capabilities. Compared to the well-established C-trifluoromethylation, N-trifluoromethylation has received lesser attention. Considering the extensive contribution of nitrogen to drug molecules, it is predicted that constructing N-trifluoromethyl (N-CF3) motifs will be of great significance in pharmaceutical and agrochemical industries. This review is mainly concerned with the synthesis of heterocycles containing this motif. In three-membered heterocycles containing the N-CF3 motif, the existing literature mostly demonstrated the synthetic strategy, as it does for four- and larger-membered heterocycles. Certain structures, such as oxaziridines, could serve as an oxidant or building blocks in organic synthesis. In five-membered heterocycles, it has been reported that N-CF3 azoles showed a higher lipophilicity and a latent increased metabolic stability and Caco-2-permeability compared with their N-CH3 counterparts, illustrating the potential of the N-CF3 motif. Various N-CF3 analogues of drugs or bioactive molecules, such as sildenafil analogue, have been obtained. In general, the N-CF3 motif is developing and has great potential in bioactive molecules or materials. Give the recent development in this motif, it is foreseeable that its synthesis methods and applications will become more and more extensive. In this paper, we present an overview of the synthesis of N-CF3 heterocycles, categorized on the basis of the number of rings (three-, four-, five-, six- and larger-membered heterocycles), and focus on the five-membered heterocycles containing the N-CF3 group.

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“…The synthesis of N-trifluoromethyl carbamoyl fluorides has also been undertaken by the group of Schoenebeck. [23][24] The authors demonstrated that such compounds could be obtained by using isothiocyanates in conjunction with silver fluoride (Scheme 4). The authors assume that difluoromethyl imines are formed through fluorinative desulfurization.…”

Section: Synthesis Of Carbamoyl Fluorides Via Difluorophosgenementioning

confidence: 99%

Modern synthesis of carbamoyl fluorides

Drapeau

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2020

Tetrahedron Letters

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N‐Trifluoromethyl Hydrazines, Indoles and Their Derivatives

Cited by 40 publications

References 78 publications

Synthesis of N-CF₃ Alkynamides and Derivatives Enabled by Ni-Catalyzed Alkynylation of N-CF₃ Carbamoyl Fluorides

Synthesis of N-CF₃ Alkynamides and Derivatives Enabled by Ni-Catalyzed Alkynylation of N-CF₃ Carbamoyl Fluorides

A Brief Review on the Synthesis of the N-CF3 Motif in Heterocycles

Modern synthesis of carbamoyl fluorides

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N‐Trifluoromethyl Hydrazines, Indoles and Their Derivatives

Cited by 40 publications

References 78 publications

Synthesis of N-CF3 Alkynamides and Derivatives Enabled by Ni-Catalyzed Alkynylation of N-CF3 Carbamoyl Fluorides

Synthesis of N-CF3 Alkynamides and Derivatives Enabled by Ni-Catalyzed Alkynylation of N-CF3 Carbamoyl Fluorides

A Brief Review on the Synthesis of the N-CF3 Motif in Heterocycles

Modern synthesis of carbamoyl fluorides

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Product

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Synthesis of N-CF₃ Alkynamides and Derivatives Enabled by Ni-Catalyzed Alkynylation of N-CF₃ Carbamoyl Fluorides

Synthesis of N-CF₃ Alkynamides and Derivatives Enabled by Ni-Catalyzed Alkynylation of N-CF₃ Carbamoyl Fluorides